Name: 14469-83-1|(5-Bromopentyl)benzene|95%
Brand: Ambeed
SKU: A589985
Price: 15.0 USD
Availability: InStock
Rating: 93 (40 reviews)

1
[ 14469-83-1 ]
[ 100129-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid at -50℃;
	With nitric acid; acetic anhydride; acetic acid for 4h;	11 Synthesis of 2p-2C-NETA, 3p-2C-NETA, and 5p-2C-NETA for Antibody Targeted Radiation Cancer Therapy In this example, 2p-2C-NETA, 3p-2C-NETA, and 5p-2C-NETA were synthesized for use in RIT. The key reaction step for preparation of the bifunctional ligands involves regiospecific ring opening of an azridinium salt that was prepared from bromination of N,N′-dialkylated β amino alcohol prepared starting from Compound 1, 2 or 3. An efficient synthetic route is presented in Scheme 20. The opening of aziridinum cations by the bulky and less nucleophilic bisubstituted TACN 10 occurred at the more substituted methine carbon to provide Compound 7, 8, or 9. t-Butyl groups in 7, 8, or 9 were removed by treatment of 7, 8, or 9 with HCl(g) to provide the desired ligands.

Reference： [1]Ashley et al. [Journal of the Chemical Society, 1958, p. 3298,3308]
[2]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; ILLINOIS INSTITUTE OF TECHNOLOGY - US9115094, 2015, B2 Location in patent: Page/Page column 109; 110; 137 - 139

2
[ 10521-91-2 ]
[ 14469-83-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With allyl bromide; 1,1'-carbonyldiimidazole In acetonitrile for 1h; Heating;
97%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃;
91%	With 2,6-dimethylpyridine; tetraethylammonium bromide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate In dichloromethane at 21℃; Inert atmosphere;

89%	With phosphorus tribromide at 0 - 60℃;
86%	With hydrogen bromide at 0 - 100℃; for 12.5h;	26A Example 26A (5-Bromopentyl)benzene A solution of 416.7 ml (1.83 mol) 48% strength hydrobromic acid is mixed with 50 g (0.304 mol) of 5-phenylpentan-1-ol at 0° C. and stirred at 0° C. for 30 min. The reaction solution is then stirred at 100° C. for 12 hours. After reaction is complete, the mixture is cooled to room temperature and 200 ml of ethyl acetate are added. After extraction, the organic phase is separated off, washed with saturated sodium bicarbonate solution and dried over sodium sulfate. After filtration, the filtrate is is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane). 59.4 g (0.26 mol, 86% yield) of a colorless liquid are obtained. 1H-NMR (300 MHz, CDCl3, δ/ppm): 7.32-7.22 (2H, m), 7.21-7.11 (3H, m), 3.40 (2H, t), 2.61 (2H, t), 1.97-1.81 (2H, m), 1.72-1.58 (2H, m), 1.56-1.39 (2H, m). MS (CI): 226 (M+).
86%	With hydrogen bromide In water at 0 - 100℃;	18.A Example 18A (5-Bromopentyl)benzene At 0° C., 50 g (0.304 mmol) of 5-phenylpentan-1-ol are added to a solution of 416.7 ml (1.83 mol) of 48% strength hydrobromic acid, and the mixture is stirred at 0° C. for 30 min. The reaction solution is then stirred at 100° C. for 12 hours. After complete conversion, the mixture is cooled to room temperature and 200 ml of ethyl acetate are added. After extraction, the organic phase is separated off, washed with saturated sodium bicarbonate solution and dried over sodium sulfate. After filtration, the filtrate is concentrated to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane). This gives 59.4 g (0.26 mol, 86% of theory) of a colorless liquid. 1H-NMR (300 MHz, CDCl3, δ/ppm): 7.32-7.22 (2H, m), 7.21-7.11 (3H, m), 3.40 (2H, t), 2.61 (2H, t), 1.97-1.81 (2H, m), 1.72-1.58 (2H, m), 1.56-1.39 (2H, m). MS (CI): 226 [M+].
86%	With hydrogen bromide In water at 0 - 10℃; for 12.5h;	1A Example 1A; (5-Bromopentyl)benzene 50 g (0.304 mol) of 5-phenylpentan-1-ol are added to a solution of 416.7 ml (1.83 mol) of 48% strength hydrobromic acid at 0° C., and the mixture is stirred at 0° C. for 30 min. The reaction solution is subsequently stirred at 10° C. for 12 hours. After reaction is complete, the mixture is cooled to room temperature and mixed with 200 ml of ethyl acetate. After extraction, the organic phase is separated off, washed with saturated sodium bicarbonate solution and dried over sodium sulphate. After filtration, the filtrate is evaporated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane). 59.4 g (0.26 mol, 86% yield) of a colourless liquid are obtained.1H-NMR (300 MHz, CDCl3, δ/ppm): 7.32-7.22 (2H, m), 7.21-7.11 (3H, m), 3.40 (2H, t), 2.61 (2H, t), 1.97-1.81 (2H, m), 1.72-1.58 (2H, m), 1.56-1.39 (2H, m).MS (CI): m/z=226 (M+).
86%	With hydrogen bromide In water at 0 - 100℃; for 12.5h;	1A Example 1A(5-Bromopentyl)benzene At 0° C., 50 g (0.304 mol) of 5-phenylpentan-1-ol are added to a solution of 416.7 ml (1.83 mol) of 48% strength hydrobromic acid, and the mixture is stirred at 0° C. for 30 min. The reaction solution is then stirred at 100° C. for 12 hours. After the reaction has gone to completion, the mixture is cooled to room temperature, and 200 ml of ethyl acetate are added. After extraction, the organic phase is separated off, washed with saturated sodium bicarbonate and dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane). This gives 59.4 g (0.26 mol, 86% of theory) of a colorless liquid.1H-NMR (300 MHz, CDCl3, δ/ppm): 7.32-7.22 (2H, m), 7.21-7.11 (3H, m), 3.40 (2H, t), 2.61 (2H, t), 1.97-1.81 (2H, m), 1.72-1.58 (2H, m), 1.56-1.39 (2H, m).MS (CI): m/z=226 (M+).
86%	With hydrogen bromide In water at 0 - 100℃;	1.A; 26.A A solution of 416.7 ml (1.83 mol) 48% strength hydrobromic acid is mixed with 50 g (0.304 mol) of 5-phenylpentan-1-ol at 0° C. and stirred at 0° C. for 30 min. The reaction solution is then stirred at 100° C. for 12 hours. After reaction is complete, the mixture is cooled to room temperature and 200 ml of ethyl acetate are added. After extraction, the organic phase is separated off, washed with saturated sodium bicarbonate solution and dried over sodium sulfate. After filtration, the filtrate is is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane). 59.4 g (0.26 mol, 86% of theory) of a colorless liquid are obtained.1H-NMR (300 MHz, CDCl3, δ/ppm): 7.32-7.22 (2H, m), 7.21-7.11 (3H, m), 3.40 (2H, t), 2.61 (2H, t), 1.97-1.81 (2H, m), 1.72-1.58 (2H, m), 1.56-1.39 (2H, m).MS (CI): 226 (M+).
70%	With carbon tetrabromide; triphenylphosphine In dichloromethane for 0.5h;
66%	With phosphorus tribromide
62%	With phosphorus tribromide at 100℃; for 1.5h;
56%	With pyridine; phosphorus tribromide In benzene at 25℃; for 21h;
49%	With phosphorus tribromide In diethyl ether at 20℃; for 24h;
40%	With phosphorus tribromide In diethyl ether for 6h; Heating;
	With hydrogen bromide
	With phosphorus; sulfuric acid; hydrogen bromide
	With phosphorus tribromide
	With sulfurous dibromide; chloroform
	With hydrogen bromide
	With sulfuric acid; hydrogen bromide
	With sulfuric acid; hydrogen bromide at 115℃; for 4h;
	With phosphorus tribromide
	With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.416667h;
	With carbon tetrabromide; triphenylphosphine In dichloromethane
	With carbon tetrabromide; triphenylphosphine In dichloromethane
	With phosphorus tribromide In chloroform	9.a (a) (a) Synthesis of 5-phenylpentyl bromide A 1.8 g (6.7 mmol) amount of phosphorus tribromide was added to a chloroform solution (20 ml) of 3.3 g (20 mmol) of 5-phenyl-1-pentanol and the resulting solution was heated at reflux for 4 hours. When the reaction was traced by TLC, the starting materials were found to still remain in the reaction mixture, and so 0.2 g of phosphorus tribromide was further added and heated at reflux. Afterwards, the reaction solution was washed with water and dried with anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. Thus, 4.30 g of a crude 5-phenylpentyl bromide was obtained.
	With hydrogen bromide	R.12 REFERENCE EXAMPLE 12 STR42 REFERENCE EXAMPLE 12 STR42 A mixture of 20 g of 5-phenylpentan-1-ol and 30 ml of 47% hydrobromic acid was refluxed for 6 hours. The reaction mixture was cooled and extracted with n-hexane The extract was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:n-hexane-ethyl acetate=100:1) to give 16.87 g of 1-bromo-5-phenylpentane. NMR (CDCl3) δ: 1.28~2.03 (6H, m), 2.63 (2H, t), 3.42 (2H, t), 7.08~7.40 (5H, m) MS: m/z 228 (M+ +1)
	With sulfuric acid; hydrogen bromide In water
	With phosphorus tribromide; sodium hydrogencarbonate In 1,4-dioxane; n-heptane; water; ethyl acetate	56.1 Step 1 Step 1 1-Bromo-5-phenylpentane Phosphorus tribromide (4.7 ml, 49.8 mmol) was added dropwise to a solution of 5-phenylpentan-1-ol (3 ml, 17.8 mmol) in dioxane (70 ml). The reaction mixture was stirred for 2 hours at room temperature. Another portion of phosphorus tribromide (4.7 m. 49.8 mmol) was added. The reaction mixture was stirred for 16 h at room temprature. It was cooled to 0° C. Water (60 ml) was added dropwise. The reaction mixture was diluted with ethyl acetate (100 ml). The phases were separated. The aqueous phase was extracted with ethyl acetate (2*100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (50 g), using ethyl acetate/heptane (1:10) as eluent, to give 1.35 g of 1-bromo-5-phenylpentane. 1H-NMR (CDCl3): δ 1.50 (m, 2 H); 1.70 (m, 2 H); 1.90 (m, 2 H); 2.60 (m, 2 H); 3.40 (m, 2 H); 7.10 (m, 3 H); 7.30 (m, 2 H).
	With sulfuric acid; hydrogen bromide In water
	With N-Bromosuccinimide; triphenylphosphine In dichloromethane	11 Synthesis of 2p-2C-NETA, 3p-2C-NETA, and 5p-2C-NETA for Antibody Targeted Radiation Cancer Therapy In this example, 2p-2C-NETA, 3p-2C-NETA, and 5p-2C-NETA were synthesized for use in RIT. The key reaction step for preparation of the bifunctional ligands involves regiospecific ring opening of an azridinium salt that was prepared from bromination of N,N′-dialkylated β amino alcohol prepared starting from Compound 1, 2 or 3. An efficient synthetic route is presented in Scheme 20. The opening of aziridinum cations by the bulky and less nucleophilic bisubstituted TACN 10 occurred at the more substituted methine carbon to provide Compound 7, 8, or 9. t-Butyl groups in 7, 8, or 9 were removed by treatment of 7, 8, or 9 with HCl(g) to provide the desired ligands.
8.99 g	With carbon tetrabromide; triphenylphosphine In acetonitrile at 20℃; for 2h;

Reference： [1]Kamijo, Tetsuhide; Harada, Hiromu; Iizuka, Kinji [Chemical and pharmaceutical bulletin, 1983, vol. 31, # 11, p. 4189 - 4192]
[2]Furuta, Kyoji; Tomokiyo, Keiichiro; Tien Kuo; Ishikawa, Toshihisa; Suzuki, Masaaki [Tetrahedron, 1999, vol. 55, # 24, p. 7529 - 7540]
[3]Pouliot, Marie-France; Mahe, Olivier; Hamel, Jean-Denys; Desroches, Justine; Paquin, Jean-Francois [Organic Letters, 2012, vol. 14, # 21, p. 5428 - 5431,4]
[4]Beauglehole; Baker; Scammells [Journal of Medicinal Chemistry, 2000, vol. 43, # 26, p. 4973 - 4980]
[5]Current Patent Assignee: BAYER AG - US2009/227640, 2009, A1 Location in patent: Page/Page column 39
[6]Current Patent Assignee: BAYER AG - US2009/286882, 2009, A1 Location in patent: Page/Page column 17
[7]Current Patent Assignee: BAYER AG - US2010/29772, 2010, A1 Location in patent: Page/Page column 14
[8]Current Patent Assignee: BAYER AG - US2010/168240, 2010, A1 Location in patent: Page/Page column 12
[9]Current Patent Assignee: BAYER AG - US2009/215843, 2009, A1 Location in patent: Page/Page column 17-18
[10]Mori, Mattia; Vignaroli, Giulia; Cau, Ylenia; Dinic̈, Jelena; Hill, Richard; Rossi, Matteo; Colecchia, David; Pešic̈, Milica; Link, Wolfgang; Chiariello, Mario; Ottmann, Christian; Botta, Maurizio [ChemMedChem, 2014, vol. 9, # 5, p. 973 - 983]
[11]Maercker, Adalbert; Passlack, Michael [Chemische Berichte, 1982, vol. 115, # 2, p. 540 - 577]
[12]Kroon, Johannes M.; Koehorst, Robert B. M.; Van Dijk, Marinus; Sanders, Georgine M.; Sudhoelter, Ernst J. R. [Journal of Materials Chemistry, 1997, vol. 7, # 4, p. 615 - 624]
[13]Marcinek, Andrzej; Platz, Matthew S.; Chan, Stephen Y.; Floresca, Rey; Rajagopalan, Krishnan; et al. [Journal of Physical Chemistry, 1994, vol. 98, # 2, p. 412 - 419]
[14]Hulshof, Janneke W.; Vischer, Henry F.; Verheij, Mark H.P.; Fratantoni, Silvina A.; Smit, Martine J.; de Esch, Iwan J.P.; Leurs, Rob [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 21, p. 7213 - 7230]
[15]Van der Mey; Hatzelmann; Van Klink; Van der Laan; Sterk; Thibaut; Ulrich; Timmerman [Journal of Medicinal Chemistry, 2001, vol. 44, # 16, p. 2523 - 2535]
[16]Truce; Wise [Journal of the American Chemical Society, 1950, vol. 72, p. 2300]
[17]Huisgen et al. [Justus Liebigs Annalen der Chemie, 1954, vol. 586, p. 1,4][Chemische Berichte, 1957, vol. 90, p. 1946,1950]
[18]Truce; Milionis [Journal of the American Chemical Society, 1952, vol. 74, p. 974,975] Skinner et al. [Journal of Organic Chemistry, 1956, vol. 21, p. 1330]
[19]Oae; VanderWerf [Journal of the American Chemical Society, 1953, vol. 75, p. 5037]
[20]Shklyaev,V.S.; Chekryshkin,Yu.S. [Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 74 - 76][Zhurnal Organicheskoi Khimii, 1968, vol. 4, p. 79 - 8] v. Braun; Deutsch; Schmatloch [Chemische Berichte, 1912, vol. 45, p. 1255]
[21]Thomas,J.; Marlow,W. [Journal of Medicinal Chemistry, 1963, vol. 6, p. 107 - 111] Collins,R.F.; Davis,M. [Journal of the Chemical Society, 1961, p. 1863 - 1879]
[22]Lynch,E.R.; McCall,E.B. [Journal of the Chemical Society, 1960, p. 1254 - 1262]
[23]Wild,R.; Hesse,M. [Helvetica Chimica Acta, 1974, vol. 57, p. 452 - 464] Hubert,A.J. [Journal of the Chemical Society C: Organic, 1967, p. 235 - 238]
[24]Gribble, Andrew D.; Dolle, Roland E.; Shaw, Antony; McNair, David; Novelli, Riccardo; Novelli, Christine E.; Slingsby, Brian P.; Shah, Virendra P.; Tew, David; Saxty, Barbara A.; Allen, Mark; Groot, Pieter H.; Pearce, Nigel; Yates, John [Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3569 - 3584]
[25]Torisawa; Nishi; Minamikawa [Bioorganic and medicinal chemistry letters, 2001, vol. 11, # 20, p. 2787 - 2789]
[26]Torisawa, Yasuhiro; Nishi, Takao; Minamikawa, Jun-ichi [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 8, p. 2583 - 2587]
[27]Current Patent Assignee: AJINOMOTO COMPANY INC - US5231105, 1993, A
[28]Current Patent Assignee: ASTELLAS PHARMA INC. - US4987132, 1991, A
[29]Location in patent: body text Maslowska-Lipowicz, Iwona; Figlus, Marek; Zuiderveld, Obbe P.; Walczynski, Krzysztof [Archiv der Pharmazie, 2008, vol. 341, # 12, p. 762 - 773] Location in patent: body text Frymarkiewicz, Anna; Walczynski, Krzysztof [European Journal of Medicinal Chemistry, 2009, vol. 44, # 4, p. 1674 - 1681]
[30]Current Patent Assignee: VTV THERAPEUTICS INC. - US2001/49385, 2001, A1
[31]Guryn, Roman; Staszewski, Marek; Walczynski, Krzysztof [Medicinal Chemistry Research, 2013, vol. 22, # 8, p. 3640 - 3652]
[32]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES; ILLINOIS INSTITUTE OF TECHNOLOGY - US9115094, 2015, B2 Location in patent: Page/Page column 109; 110; 137 - 139
[33]Shiely, Amy E.; Clarke, Leslie-Ann; Flynn, Christopher J.; Buckley, Aoife M.; Ford, Alan; Lawrence, Simon E.; Maguire, Anita R. [European Journal of Organic Chemistry, 2018, vol. 2018, # 19, p. 2277 - 2289]

3
[ 14469-83-1 ]
[ 106-95-6 ]
[ 35008-87-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: (5-bromopentyl)benzene With magnesium In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; Stage #2: With [2,2]bipyridinyl; copper(l) iodide In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #3: allyl bromide In tetrahydrofuran at 25℃; Inert atmosphere;
	(i) Mg, Et₂O, (ii) /BRN= 605308/; Multistep reaction;

Reference： [1]Murai, Masahito; Nishimura, Kengo; Takai, Kazuhiko [Chemical Communications, 2019, vol. 55, # 19, p. 2769 - 2772]
[2]Chevalier,P. et al. [Bulletin de la Societe Chimique de France, 1975, p. 2254 - 2258]

4
[ 14469-83-1 ]
[ 67686-01-5 ]
1-Benzyl-4-(5-phenyl-pentyloxymethyl)-piperidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4344 - 4361

5
[ 14469-83-1 ]
[ 1074-82-4 ]
[ 53429-14-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	In N,N-dimethyl-formamide at 25℃; for 92h;
76%	In N,N-dimethyl-formamide for 15h; Inert atmosphere; Heating;
	In N,N-dimethyl-formamide for 1.5h; Heating;

Reference： [1]Marcinek, Andrzej; Platz, Matthew S.; Chan, Stephen Y.; Floresca, Rey; Rajagopalan, Krishnan; et al. [Journal of Physical Chemistry, 1994, vol. 98, # 2, p. 412 - 419]
[2]Guo, Shuo; AbuSalim, Deyaa I.; Cook, Silas P. [Journal of the American Chemical Society, 2018, vol. 140, # 39, p. 12378 - 12382]
[3]Lever, O. William; Bell, Lawrence N.; McGuire, H. Michael; Ferone, Robert [Journal of Medicinal Chemistry, 1985, vol. 28, # 12, p. 1870 - 1874]

6
[ 14469-83-1 ]
[ 81631-41-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With lithium In diethyl ether at -30℃; <D10>Et2O;

Reference： [1]Maercker, Adalbert; Passlack, Michael [Chemische Berichte, 1982, vol. 115, # 2, p. 540 - 577]

7
[ 14469-83-1 ]
[ 94-09-7 ]
[ 61439-74-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	In N,N,N,N,N,N-hexamethylphosphoric triamide at 125℃; for 24h;

Reference： [1]Albright; DeVries; Largis; Miner; Reich; Schaffer; Shepherd; Upeslacis [Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1378 - 1393]

8
[ 524-38-9 ]
[ 14469-83-1 ]
2-(5-Phenyl-pentyloxy)-isoindole-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydride In N,N-dimethyl-formamide at 70℃; for 3h;
	With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; for 2h; Inert atmosphere;

Reference： [1]Kim, Sunggak; Lee, Tai Au; Song, Yukwan [Synlett, 1998, # 5, p. 471 - 472]
[2]Fang, Di; Zhang, Yidan; Chen, Yiyun [Organic Letters, 2022, vol. 24, # 10, p. 2050 - 2054]

9
[ 14469-83-1 ]
[ 5418-86-0 ]
[ 183592-72-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;

Reference： [1]Furuta, Satoru; Kuroboshi, Manabu; Hiyama, Tamejiro [Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 8, p. 1939 - 1951]

10
[ 14469-83-1 ]
[ 98-88-4 ]
[ 213267-08-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With aluminium trichloride In dichloromethane at 0℃; for 22.5h;

Reference： [1]Furuta, Kyoji; Tomokiyo, Keiichiro; Tien Kuo; Ishikawa, Toshihisa; Suzuki, Masaaki [Tetrahedron, 1999, vol. 55, # 24, p. 7529 - 7540]

11
[ 14469-83-1 ]
[ 99-76-3 ]
[ 158771-44-9 ]

Yield	Reaction Conditions	Operation in experiment
47%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 8h;
	With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 100℃; for 24h;

Reference： [1]Igarashi, Susumu; Kimura, Takenori; Naito, Ryo; Hara, Hiromu; Fujii, Masahiro; Koutoku, Hiroshi; Oritani, Hiroyuki; Mase, Toshiyasu [Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 8, p. 1073 - 1080]
[2]Bajzíková, Kvetoslava; Svoboda, Jiří; Novotná, Vladimíra; Pociecha, Damian; Gorecka, Ewa [New Journal of Chemistry, 2017, vol. 41, # 11, p. 4672 - 4679]

12
[ 14469-83-1 ]
[ 170147-91-8 ]
[ 170147-60-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 3-chloro-4-(1H-indol-5-yloxy)benzonitrile With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.666667h; Stage #2: (5-bromopentyl)benzene In dimethyl sulfoxide at 20℃; for 2h;

Reference： [1]Igarashi, Susumu; Inami, Hiroshi; Hara, Hiromu; Fujii, Masahiro; Koutoku, Hiroshi; Oritani, Hiroyuki; Mase, Toshiyasu [Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 3, p. 382 - 388]

13
[ 110-89-4 ]
[ 14469-83-1 ]
[ 146403-57-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate; potassium iodide In 1,2-dimethoxyethane for 12h; Heating;

Reference： [1]Ablordeppey, Seth Y.; Fischer, James B.; Glennon, Richard A. [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 8, p. 2105 - 2111]

14
[ 14469-83-1 ]
4-(5-Bromopentyl)benzenesulfonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With chlorosulfonic acid In chloroform at 20℃; for 16h;

Reference： [1]Beauglehole; Baker; Scammells [Journal of Medicinal Chemistry, 2000, vol. 43, # 26, p. 4973 - 4980]

15
[ 14469-83-1 ]
[ 484689-19-2 ]

Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: (5-bromopentyl)benzene With magnesium In diethyl ether for 4h; Heating; Stage #2: With cadmium(II) chloride at 0℃; for 2h; Stage #3: With phosphorus trichloride In diethyl ether at 20℃; for 2.5h;
	Stage #1: (5-bromopentyl)benzene With magnesium Stage #2: With cadmium(II) chloride Stage #3: With phosphorus trichloride at -80℃;

Reference： [1]Amberg, Stefan; Engels, Joachim W. [Helvetica Chimica Acta, 2002, vol. 85, # 8, p. 2503 - 2517]
[2]Amberg; Engels [Nucleosides, nucleotides and nucleic acids, 2001, vol. 20, # 4-7, p. 1275 - 1278]

16
[ 14469-83-1 ]
cis-2-cycloheptyl-4-(3-hydroxy-4-methoxyphenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one [ No CAS ]
cis-2-cycloheptyl-4-[4-methoxy-3-(5-phenylpentyloxy)phenyl]-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate In 1-methyl-pyrrolidin-2-one at 60℃; for 5h;

Reference： [1]Van der Mey; Hatzelmann; Van Klink; Van der Laan; Sterk; Thibaut; Ulrich; Timmerman [Journal of Medicinal Chemistry, 2001, vol. 44, # 16, p. 2523 - 2535]

17
[ 14469-83-1 ]
[ 538-68-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium cyanoborohydride In various solvent(s) at 80℃; for 1h;
78%	With sodium tetrahydroborate In 1-methyl-pyrrolidin-2-one at 20℃; for 3h;

Reference： [1]Torisawa; Nishi; Minamikawa [Bioorganic and medicinal chemistry letters, 2001, vol. 11, # 20, p. 2787 - 2789]
[2]Torisawa, Yasuhiro; Nishi, Takao; Minamikawa, Jun-ichi [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 8, p. 2583 - 2587]

18
[ 3973-62-4 ]
[ 14469-83-1 ]
1-(5-Phenylpentyl)-3-phenylpiperidine [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry,2002,vol. 10,p. 2759 - 2765

19
[ 13603-25-3 ]
[ 14469-83-1 ]
1-(5-Phenylpentyl)-3-benzylpiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide In 1,2-dimethoxyethane Heating;

Reference： [1]Ablordeppey, Seth Y; Fischer, James B; Law; Glennon, Richard A [Bioorganic and medicinal chemistry, 2002, vol. 10, # 8, p. 2759 - 2765]

20
[ 14469-83-1 ]
[ 22583-90-0 ]
N-(5-phenylpentyl)-N-methyl-2-aminotetraline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate In 1,2-dimethoxyethane for 5h; Heating;

Reference： [1]Ablordeppey, Seth Y; Fischer, James B; Law; Glennon, Richard A [Bioorganic and medicinal chemistry, 2002, vol. 10, # 8, p. 2759 - 2765]

21
[ 14469-83-1 ]
[ 245-08-9 ]
1-(5-phenyl-pentyl)-5<i>H</i>-pyrido[3,2-<i>b</i>]indol-1-ium; bromide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1999,vol. 9,p. 118 - 132

22
[ 14469-83-1 ]
[ 283-24-9 ]
3-(5-phenylpentyl)-3-azabicyclo[3.2.2]nonane hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; potassium iodide In 1,2-dimethoxyethane for 5h; Heating;

Reference： [1]Ablordeppey, Seth Y; Fischer, James B; Law; Glennon, Richard A [Bioorganic and medicinal chemistry, 2002, vol. 10, # 8, p. 2759 - 2765]

23
[ 14469-83-1 ]
[ 4294-57-9 ]
[ 613-33-2 ]
[ 538-68-1 ]
[ 1075-74-7 ]
[ 38425-25-1 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 1297 - 1299
[2]Organic Letters,2004,vol. 6,p. 1297 - 1299
[3]Organic Letters,2004,vol. 6,p. 1297 - 1299

24
[ 14469-83-1 ]
[ 540-37-4 ]
4-(5-phenyl-pentylsulfanyl)-phenylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: p-aminoiodobenzene With tert.-butyl lithium; isopropylmagnesium chloride In tetrahydrofuran; diethyl ether; pentane at -78℃; for 0.5h; Stage #2: With sulfur In tetrahydrofuran; diethyl ether; pentane at -78 - 20℃; for 0.5h; Stage #3: (5-bromopentyl)benzene In tetrahydrofuran; diethyl ether; pentane at 0 - 20℃;

Reference： [1]Ham, Jungyeob; Cho, Sung Jin; Ko, Jaeyoung; Chin, Jungwook; Kang, Heonjoong [Journal of Organic Chemistry, 2006, vol. 71, # 15, p. 5781 - 5784]

25
[ 14469-83-1 ]
[ 496-69-5 ]
2-(5-phenylpentylthio)-4-fluorophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 2-bromo-4-fluoro-phenol With tert.-butyl lithium; isopropylmagnesium chloride In tetrahydrofuran; pentane at -78℃; for 0.5h; Stage #2: (5-bromopentyl)benzene With sulfur at -78 - 20℃;

Reference： [1]Ko, Jaeyoung; Ham, Jungyeob; Yang, Inho; Chin, Jungwook; Nam, Sang-Jip; Kang, Heonjoong [Tetrahedron Letters, 2006, vol. 47, # 39, p. 7101 - 7106]

26
[ 14469-83-1 ]
[ 39512-49-7 ]
VUF 5752 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium carbonate; sodium iodide In acetonitrile Heating;

Reference： [1]Hulshof, Janneke W.; Vischer, Henry F.; Verheij, Mark H.P.; Fratantoni, Silvina A.; Smit, Martine J.; de Esch, Iwan J.P.; Leurs, Rob [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 21, p. 7213 - 7230]

27
[ 14469-83-1 ]
[ 554-84-7 ]
[ 1007863-89-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 90℃; for 4h;	1 Potassium carbonate (1.2 g, 8.7 mmol) was added to a stirred suspension of 3- nitrophenoi (0,8 g, 5,8 mmoi), (S-bτomo-perityi)-benzene ( . .32 g, 5.8 mmoi), and potassium iodide (0.96 g, 5.8 mmol) in λ'-methylpyroiidiiione (I S mL). The mixture was stirred at 9ffC for 4 hours. After the reaction mixture was cooled to the room temperature, if was quenched with wafer (30 mL) followed by extraction with ethyl acetate (30 mL. x 3). The organic layers were combined, washed with brine, and concentrated under vacuum. The residue thus obtained was subjected to column chromatography on silica gel to give i~nitro-3-(5~pheoylpentoxy)benzeoe ( 1.4 g, 4.93 mmol, yield: 85%) as colotiess oil.Tin (Ii) chloride (5.57 g. 24.7 mmol) was added to a solution of i -nitro-3-(5- pheny]peoio.y)benzene (1.4 g, 4.93 minof) in 35 ml. ethane] . The reaction mixture was stirred at 7011C tor 2 hours. After the reaction mixture was cooled to room temperature, a saturated sodium bicarbonate aqueous solution { 50 mL) was added. The resultant mixture was extracted with ethyl acetate (2 x 50 ml..}. The combined organic phases were washed with brine, dried over anhydrous MgSOj, and concentrated to give a crude product as a white solid. The crude product was purified by silica gel column chromatography euting with ethyl acetate-w-hexarte to give 3-(5- phetiyl-penryloxy j-pherryiaroine ( 1.03 g, 4.04 mmoi, yield: 82%) as a white solid,A solution of 3~(5-phenyl-pentyloxy)-phenyIamine (200 mg, ,02 mmol) and thiocarbonyi diimidazole (TCDl, 190 mg, 1.06 mmol) in diehiororøethane ( 10 nil.) was stirred at room temperature for 2 hours. After a 25% aqueous ammonia solution (2.0 mL. excess) was added, the reaction mixture was stirred at room temperature overnight. The solvent was removed and ihen the residue thus obtained was purified by silica gel column chromatography eiining with methanoi-dichioromethane to give j3-(5-phenyi-pentyloxy)-pbenjfl]-thfoui"ea (compound 1) (273 mg, 0.8? mmol, yield: 85 %) as a white solid. Ei-MS (VI-H ); 315.
	With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 90℃; for 3h;

Reference： [1]Current Patent Assignee: NATIONAL HEALTH RESEARCH INSTITUTES - WO2008/22204, 2008, A2 Location in patent: Page/Page column 40-41
[2]Location in patent: scheme or table Kang, Iou-Jiun; Wang, Li-Wen; Lee, Chung-Chi; Lee, Yen-Chun; Chao, Yu-Sheng; Hsu, Tsu-An; Chern, Jyh-Haur [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 7, p. 1950 - 1955]

28
[ 14469-83-1 ]
[ 68621-88-5 ]
[ 1007864-12-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 90℃; for 4h;	15 (BOCfeO (K)J g. 46.3 rniiiftl) was added to a solution of benzene- i ,3-diamjne (5,0 g, 46,3 rømoi) in dichlorornethane (SO mL}, The reaction mixture was stirred at room temperature for 60 hours. The reaction mixture was quenched with water (30 mL). followed by extraction with ethyl acetate (30 mi... x 3). The organic layers were combined, washed with brine, and concentrated under vacuum. The residue thus obtained was subjected to column chromatography on silica gel to give (3-amino- phenyl)-carbamic acid tat-hυtyi ester (4.34 g, 20.8 mniol, yield: 45%) as a white solid. Potassium carbonate (0.6 g 4,35 mmo) was added to a stirred suspension of(3-ammo-phenylj-carbamie acid tert-butyi ester (0.6 g. 2.9 mmol), (5-brotno-pentyl)- benzene (0.66 g, 2.9 mmol), and potassium iodide (0.48 g, 2.9 nimαi) in N- methylpyrolidiϖotie ( 14 mL). The reaction mixture was stirred at 9O0C tor 4 hours. It was quenched with water (30 mL), followed by extraction with ethyl acetate (30 mL x 3). The organic layers were combined, washed with brine, and concentrated under vacuum. The residue thus obtained was subjected to column chromatography on silica gel to give [3-(5-phenyi-penty.amino)-phenyi]-carbamic acid tert-bυtyl ester < 802 nig, 2.26 mmol, yield: 78%) as yellow oil.Trifluoroaeetic acid (TFA, 2.0 mL. 263 mmol) was added to a solution of [3- ('5-pherjy.-penr.y1fimsno)-phenyl]-cfirbamic acid tert-butyi ester {802 rag, 2.26 mrao.) in 10 rat dichloromethane. The reaction mixture was stirred at room temperature for hour. It was then quenched with water (30 mL). followed by extraction with ethyl acetate (30 mL x 3 ). The organic layers were combined, washed with brine, and concentrated under vacuum. The residue thus obtained was subjected to column chromatography on silica gei ks give N -(5-phe«yi-pentyI )- benzene- 1,3- dianiine (529 mg. 2.08 mmol, yield: 92%) as light yellow solid.5 A soiuon of N-(5-pheiiy1-penιyi}-benzene-K3-diami)ie (89 ing, 0.4 mmol) and thiocarbonyl diimidazoie (TCDl, 74 mg. 0,42 mmot) in dichloroniethane (4 ml.) was stirred at room temperature for 2 hours. After a 25% aqueous ammonia solution (2.0 nil.., excess} was added, the reaction mixture was stirred at room temperature overnight. The solvent was then removed and the residue thus obtained was purified 10 by silica gel column chromatography dating with mcthanoi-dichloromethane to give \|3-(5-phenyi-peotylamiiioVphenyi]-{.hioιsre3 (compound 37.) ( 5 13 mg. 036 mmol, yield: 90%; as a white solid

Reference： [1]Current Patent Assignee: NATIONAL HEALTH RESEARCH INSTITUTES - WO2008/22204, 2008, A2 Location in patent: Page/Page column 45-46

29
5-phenyl-4-pentenoic acid [ No CAS ]
[ 14469-83-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: diethyl ether; methanol 2: DIBAL-H / CH₂Cl₂ / 0.5 h / 0 °C 3: H₂ / PtO₂ / methanol / 2585.7 Torr 4: NBS, Ph₃P / CH₂Cl₂ / 0.42 h / 0 - 20 °C

Reference： [1]Gribble, Andrew D.; Dolle, Roland E.; Shaw, Antony; McNair, David; Novelli, Riccardo; Novelli, Christine E.; Slingsby, Brian P.; Shah, Virendra P.; Tew, David; Saxty, Barbara A.; Allen, Mark; Groot, Pieter H.; Pearce, Nigel; Yates, John [Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3569 - 3584]

30
[ 37464-85-0 ]
[ 14469-83-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: DIBAL-H / CH₂Cl₂ / 0.5 h / 0 °C 2: H₂ / PtO₂ / methanol / 2585.7 Torr 3: NBS, Ph₃P / CH₂Cl₂ / 0.42 h / 0 - 20 °C

Reference： [1]Gribble, Andrew D.; Dolle, Roland E.; Shaw, Antony; McNair, David; Novelli, Riccardo; Novelli, Christine E.; Slingsby, Brian P.; Shah, Virendra P.; Tew, David; Saxty, Barbara A.; Allen, Mark; Groot, Pieter H.; Pearce, Nigel; Yates, John [Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3569 - 3584]

31
5-phenyl-4-penten-1-ol [ No CAS ]
[ 14469-83-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / PtO₂ / methanol / 2585.7 Torr 2: NBS, Ph₃P / CH₂Cl₂ / 0.42 h / 0 - 20 °C

Reference： [1]Gribble, Andrew D.; Dolle, Roland E.; Shaw, Antony; McNair, David; Novelli, Riccardo; Novelli, Christine E.; Slingsby, Brian P.; Shah, Virendra P.; Tew, David; Saxty, Barbara A.; Allen, Mark; Groot, Pieter H.; Pearce, Nigel; Yates, John [Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3569 - 3584]

32
[ 100-52-7 ]
[ 14469-83-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) NaCH₂SOCH₃ / 1.) DMSO, RT, 30 min, 2.) DMSO, RT, 1 h 2: diethyl ether; methanol 3: DIBAL-H / CH₂Cl₂ / 0.5 h / 0 °C 4: H₂ / PtO₂ / methanol / 2585.7 Torr 5: NBS, Ph₃P / CH₂Cl₂ / 0.42 h / 0 - 20 °C

Reference： [1]Gribble, Andrew D.; Dolle, Roland E.; Shaw, Antony; McNair, David; Novelli, Riccardo; Novelli, Christine E.; Slingsby, Brian P.; Shah, Virendra P.; Tew, David; Saxty, Barbara A.; Allen, Mark; Groot, Pieter H.; Pearce, Nigel; Yates, John [Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3569 - 3584]

33
[ 14469-83-1 ]
[ 167113-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) EtONa / 1.) ethanol, 50 deg C, 1 h, 2.) ethanol, reflux, overnight 2: 98.2 percent / aq. KOH / ethanol / 3 h / Ambient temperature 3: 100 percent / dioxane / Heating 4: 95.1 percent / aq. KOH / ethanol / 1.5 h / Ambient temperature 5: 90.7 percent / CoCl₂ / H₂O / 72 h / 37 °C / pH 7.6, acylase

Reference： [1]Plummet; Shahripour; Kaltenbronn; Lunney; Steinbaugh; Hamby; Hamilton; Sawyer; Humblet; Doherty; Taylor; Hingorani; Barley; Rapundalo [Journal of Medicinal Chemistry, 1995, vol. 38, # 15, p. 2893 - 2905]

34
[ 14469-83-1 ]
L-2-(Boc-amino)-7-phenylheptanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 1.) EtONa / 1.) ethanol, 50 deg C, 1 h, 2.) ethanol, reflux, overnight 2: 98.2 percent / aq. KOH / ethanol / 3 h / Ambient temperature 3: 100 percent / dioxane / Heating 4: 95.1 percent / aq. KOH / ethanol / 1.5 h / Ambient temperature 5: 90.7 percent / CoCl₂ / H₂O / 72 h / 37 °C / pH 7.6, acylase 6: 100 percent / 2 N aq. NaOH / dioxane / Ambient temperature

Reference： [1]Plummet; Shahripour; Kaltenbronn; Lunney; Steinbaugh; Hamby; Hamilton; Sawyer; Humblet; Doherty; Taylor; Hingorani; Barley; Rapundalo [Journal of Medicinal Chemistry, 1995, vol. 38, # 15, p. 2893 - 2905]

35
[ 14469-83-1 ]
[ 120755-16-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) Mg / 1.) THF, 2.) 0 deg C, THF 2: tetrahydrofuran / Ambient temperature 3: 65 percent / O₂ / Rose Bengal / tetrahydrofuran / 4 h / -78 °C / Irradiation
	Multi-step reaction with 4 steps 1: 1.) Mg / 1.) THF, 2.) 0 deg C, THF 2: tetrahydrofuran / Ambient temperature 3: 20 percent / O₂ / Rose Bengal / tetrahydrofuran / 4 h / -78 °C / Irradiation 4: dilute acid / Ambient temperature

Reference： [1]Lee, Gary C. M.; Syage, Elizabeth T.; Harcourt, Dale A.; Holmes, Judy M.; Garst, Michael E. [Journal of Organic Chemistry, 1991, vol. 56, # 25, p. 7007 - 7014]
[2]Lee, Gary C. M.; Syage, Elizabeth T.; Harcourt, Dale A.; Holmes, Judy M.; Garst, Michael E. [Journal of Organic Chemistry, 1991, vol. 56, # 25, p. 7007 - 7014]

36
[ 14469-83-1 ]
[ 136618-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) Mg / 1.) THF, 2.) 0 deg C, THF 2: tetrahydrofuran / Ambient temperature 3: 20 percent / O₂ / Rose Bengal / tetrahydrofuran / 4 h / -78 °C / Irradiation

Reference： [1]Lee, Gary C. M.; Syage, Elizabeth T.; Harcourt, Dale A.; Holmes, Judy M.; Garst, Michael E. [Journal of Organic Chemistry, 1991, vol. 56, # 25, p. 7007 - 7014]

37
[ 14469-83-1 ]
[ 329774-47-2 ]
[ 329774-48-3 ]

Yield	Reaction Conditions	Operation in experiment
88.8%	With potassium carbonate In acetonitrile for 18h; Heating / reflux;

Reference： [1]Current Patent Assignee: BAYER AG - EP1216225, 2005, B1 Location in patent: Page/Page column 35

38
[ 14469-83-1 ]
4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride [ No CAS ]
[ 147188-32-7 ]
5-phenylpentylmagnesium bromide [ No CAS ]
6-(5-phenylpentylsulfonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuryl dichloride; magnesium; triethylamine In diethyl ether; dichloromethane	52.a a) a) Synthesis of 6-(5-phenylpentylsulfonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine To a solution of 0.236 g (1.479 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride and 0.82 ml (5.9 mmol) of triethylamine in 30 ml of dichloromethane, a solution of 0.73 g of crude 5-phenylpentylsulfonyl chloride (obtained by adding dropwise a diethyl ether solution of 5-phenylpentylmagnesium bromide, prepared from 5.860 g (25.80 mmol) of 1-bromo-5-phenylpentane and 0.94 g (38.7 mmol) of magnesium in 150 ml of diethyl ether, to a solution of 5.15 ml (51.6 mmol) of sulfuryl chloride in 50 ml of diethyl ether under ice-cooling, followed by stirring under ice-cooling for 3 hours, filtering and washing with diethyl ether the resulting precipitate, and evaporating the combined filtrate under reduced pressure) in 10 ml of dichloromethane was added dropwise under ice-cooling, followed by stirring under ice-cooling for 1 hour. The reaction mixture was poured into aqueous sodium hydrogen carbonate and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel flush column chromatography (hexane/ethyl acetate=6/1) to yield the desired product. Yellow oil Yield 0.181 g (37%) 1 H-NMR (CDCl3, 200 MHz) δ1.355-1.495 (2H, m), 1.564 (2H, m), 1.742-1.896 (2H, m), 2.564-2.638 (4H, m), 2.889-2.967 (2H, m), 3.542 (2H, t, J=5.7 Hz), 4.365 (2H, s), 6.260 (1H, d, 1.8 Hz), 7.127-7.310 (6H, m); IR (neat) 2933, 2856, 1335, 1151, 1005, 910, 737, 700 cm-1

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US5998433, 1999, A

39
[ 14469-83-1 ]
4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride [ No CAS ]
[ 147188-32-7 ]
5-phenylpentylmagnesium bromide [ No CAS ]
[ 179060-95-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuryl dichloride; magnesium; triethylamine In diethyl ether; dichloromethane	53.a a) a) Synthesis of 5-(5-phenylpentylsulfonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine To a solution of 0.298 g (1.867 mmol) of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride and 1.30 ml (9.34 mmol) of triethylamine in 30 ml of dichloromethane, a solution of 1.38 g of crude 5-phenylpentylsulfonyl chloride (obtained by adding dropwise a diethyl ether solution of 5-phenylpentylmagnesium bromide, prepared from 5.860 g (25.80 mmol) of 1-bromo-5-phenylpentane and 0.94 g (38.7 mmol) of magnesium in 150 ml of diethyl ether, to a solution of 5.15 ml (51.6 mmol) of sulfuryl chloride in 50 ml of diethyl ether under ice-cooling, followed by stirring under ice-cooling for 3 hours, filtering and washing with diethyl ether the resulting precipitate, and evaporating the combined filtrate under reduced pressure) in 10 ml of dichloromethane was added dropwise under ice-cooling, followed by stirring under ice-cooling for 1 hour. The reaction mixture was poured into aqueous sodium hydrogen carbonate and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel flush column chromatography (hexane/ethyl acetate=6/1) to yield the desired product. Orange oil Yield 0.335 g (54%) 1 H-NMR (CDCl3, 200 MHz) δ1.348-1.487 (2H, m), 1.559-1.705 (2H, m), 1.736-1.892 (2H, m), 2.599 (2H, t, J=7.3 Hz), 2.768 (2H, t, J=5.7 Hz), 2.874-2.953 (2H, m), 3.629 (2H, t, J=5.9 Hz), 4.270 (2H, t, J=1.8 Hz), 6.225 (1H, d, J=2.0 Hz), 7.127-7.362 (6H, m); IR (neat) 2935, 2858, 1336, 1142, 1003, 893, 737, 702 cm-1

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US5998433, 1999, A

40
[ 79-43-6 ]
NaOH powder [ No CAS ]
[ 14469-83-1 ]
Li₂ CuCl₄ [ No CAS ]
[ 178670-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium In tetrahydrofuran; dibromo-1,1 octane	42 1-Bromo-13-phenyl-tridecane (93) 4.9 g (51%) 93 was obtained analogously to the preparation of 67 (example 15) as a colourless oil of melting point 158-159° C./0.15 mbar after distillation in a high vacuum from 7.48 g (27.5 mmol) dibromooctane, 7.27 g (32.1 mmol) 1-bromo-5-phenylpentane, 0.85 g (35 mmol) magnesium and 5 ml (0.5 mmol) Li2 CuCl4 (0.1 M in THF). 1.3 g (67%) 42 was obtained with a melting point of 52-53° C. from 1.7 g (5 mmol) 93 and 2.58 g (20 mmol) dichloroacetic acid as in example 9. The sodium salt was prepared from 0.8 g (2.1 mmol) 42 using 84 mg (2.1 mmol) NaOH powder. 0.7 g melting point 170° C. (decomp.)

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US5968982, 1999, A

41
[ 14469-83-1 ]
[ 25519-78-2 ]
4-(4-fluorobenzoyl)-1-(5-phenylpentyl)piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water;	(b) Synthesis of 4-(4-fluorobenzoyl)-1-(5-phenylpentyl)piperidine Fifty ml of isopropyl alcohol and 2.26 g of the crude 5-phenylpentyl bromide were added to a mixture comprising 2.4 g (9.9 mmol) of <strong>[25519-78-2]4-(4-fluorobenzoyl)piperidine hydrochloride</strong> and 2.1 g (19.8 mmol) of anhydrous sodium carbonate, and the resulting mixture was heated under reflux. The reaction was continued overnight and then the heating was stopped. The reaction mixture was concentrated under reduced pressure, and water was added thereto. This was extracted with chloroform. The resulting extract was dried with anhydrous magnesium sulfate and then the solvent was evaporated under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain the above-entitled compound. Yield: 2.18 g, 62%. TLC (CHCl3:MeOH=9:1). Rf =0.41. MS (FD, m/z) 353 (M+).

Reference： [1]Patent: US5231105,1993,A

42
[ 14469-83-1 ]
[ 105-53-3 ]
[ 78573-53-2 ]
[ 78573-51-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium In ethanol	10.d (d) (d) 5-Phenylpentylmalonic acid diethyl ester 66.8 g of 5-phenylpentylmalonic acid diethyl ester are obtained as an oil (b.p. 142° to 148° C. under 0.02 mm Hg) from 80.8 g of 1-bromo-5-phenylpentane, 64.1 g of malonic acid diethyl ester and a solution of 8.2 g of sodium in 400 ml of ethanol by the procedure described in Example 5d.

Reference： [1]Current Patent Assignee: CHRANKTER HAFTUNG; TAKEDA PHARMACEUTICAL COMPANY LIMITED - US4324796, 1982, A

43
[ 74891-64-8 ]
[ 14469-83-1 ]
2-Hydroxy-4-(5-phenylpentylthio)-3-propylacetophenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium iodide; potassium carbonate In <i>N</i>-methyl-acetamide; Petroleum ether	8.a (a) (a) 2-Hydroxy-4-(5-phenylpentylthio)-3-propylacetophenone A mixture of 5-bromopentylbenzene (1.93 g), 2-hydroxy-4-mercapto-3-propylacetophenone (1.78 g), potassium carbonate (1.28 g), and potassium iodide (0.1 g) in dry dimethylformamide (60 ml) under nitrogen was heated at 60° for 20 hr. The mixture was partitioned between ethyl acetate and dilute hydrochloric acid. The organic phase was washed with water, dried and evaporated to an oil which was chromatographed on silica with a mixture of petroleum ether (bp 40°-60°) and ether (9:1) to give the sub-title compound (1.85 g), mp 82°-83°.

Reference： [1]Current Patent Assignee: SANOFI - US4424231, 1984, A

44
[ 14469-83-1 ]
[ 1092980-29-4 ]
[ 1092980-47-6 ]

Yield	Reaction Conditions	Operation in experiment
35.9%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;

Reference： [1]Location in patent: experimental part Maslowska-Lipowicz, Iwona; Figlus, Marek; Zuiderveld, Obbe P.; Walczynski, Krzysztof [Archiv der Pharmazie, 2008, vol. 341, # 12, p. 762 - 773]

45
[ 14469-83-1 ]
[ 1092980-35-2 ]
[ 1092980-59-0 ]

Yield	Reaction Conditions	Operation in experiment
40.7%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;

Reference： [1]Location in patent: experimental part Maslowska-Lipowicz, Iwona; Figlus, Marek; Zuiderveld, Obbe P.; Walczynski, Krzysztof [Archiv der Pharmazie, 2008, vol. 341, # 12, p. 762 - 773]

46
[ 14469-83-1 ]
[ 7726-45-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: (5-bromopentyl)benzene With ammonia In water at 60℃; for 24h; Stage #2: With ammonia; iodine In water at 60℃; for 4h;
76%	Stage #1: (5-bromopentyl)benzene With ammonia In water at 60℃; for 24h; Stage #2: With ammonia; iodine In water at 60℃; for 4h;

Reference： [1]Location in patent: experimental part Iida, Shinpei; Togo, Hideo [Synlett, 2008, # 11, p. 1639 - 1642]
[2]Location in patent: experimental part Iida, Shinpei; Ohmura, Ryosuke; Togo, Hideo [Tetrahedron, 2009, vol. 65, # 31, p. 6257 - 6262]

47
[ 14469-83-1 ]
[ 1149336-58-2 ]
[ 1149336-77-5 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 24h;

Reference： [1]Location in patent: experimental part Frymarkiewicz, Anna; Walczynski, Krzysztof [European Journal of Medicinal Chemistry, 2009, vol. 44, # 4, p. 1674 - 1681]

48
[ 14469-83-1 ]
[ 90-01-7 ]
[ 135055-19-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate In acetonitrile for 12h; Reflux;	27A Example 27A [2-(5-Phenylpentyloxy)phenyl]methanol A solution of 10 g (80.56 mmol) of 2-hydroxybenzyl alcohol in 200 ml of dry acetonitrile is mixed with 27.45 g (120.83 mmol) of (5-bromopentyl)benzene from Example 26A and 12.25 g (88.61 mmol) of anhydrous potassium carbonate and heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The resulting organic phase is concentrated. The crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 18.7 g (81% yield) of a colorless solid are obtained. 1H-NMR (300 MHz, DMSO-d6, o/ppm): 7.38 (1H, d), 7.31-7.10 (6H, m), 6.91 (2H, t), 4.92 (1H, t), 4.50 (2H, d), 3.95 (2H, t), 2.59 (2H, t), 1.81-1.68 (2H, m), 1.67-1.55 (2H, m), 1.52-1.36 (2H, m). MS (CI): 288 (M+NH4+), 270 (M+).
81%	With potassium carbonate In acetonitrile for 12h; Reflux;	21.A A solution of 10 g (80.56 mmol) of 2-hydroxybenzyl alcohol in 200 ml of dry acetonitrile is mixed with 27.45 g (120.83 mmol) of (5-bromopentyl)benzene and 12.25 g (88.61 mmol) of anhydrous potassium carbonate and heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 18.7 g (81% of theory) of a colorless solid are obtained.1H-NMR (300 MHz, DMSO-d6, δ/ppm): 7.38 (1H, d), 7.31-7.10 (6H, m), 6.91 (2H, t), 4.92 (1H, t), 4.50 (2H, d), 3.95 (2H, t), 2.59 (2H, t), 1.81-1.68 (2H, m), 1.67-1.55 (2H, m), 1.52-1.36 (2H, m).MS (CI): 288 (M+NH4+), 270 (M+).

Reference： [1]Current Patent Assignee: BAYER AG - US2009/227640, 2009, A1 Location in patent: Page/Page column 39-40
[2]Current Patent Assignee: BAYER AG - US2009/215843, 2009, A1 Location in patent: Page/Page column 24

49
[ 14469-83-1 ]
[ 934753-52-3 ]
[ 935253-38-6 ]

Yield	Reaction Conditions	Operation in experiment
73.4%	With potassium carbonate In acetonitrile Reflux;	62.A A solution of 127 mg (0.32 mmol) of ethyl (7E)-6-[2-(4-cyanophenyl)ethyl]-8-(2-hydroxyphenyl)oct-7-enoate in 10 ml of acetonitrile is mixed with 88.42 mg (0.39 mmol) of (5-bromopentyl)benzene and 67.25 mg (0.49 mmol) of potassium carbonate and stirred under reflux for 12 hours. After cooling, the mixture is concentrated. The residue is taken up in ethyl acetate and extracted with water. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated. The resulting residue is purified by preparative HPLC. 128 mg (0.24 mmol, 73.4% of theory) of the title compound are obtained.LC-MS (method 2): Rt=3.42 min.MS (ESIpos): m/z=538 (M+H)+.

Reference： [1]Current Patent Assignee: BAYER AG - US2009/215843, 2009, A1 Location in patent: Page/Page column 37-38

50
[ 14469-83-1 ]
[ 934738-20-2 ]
[ 935253-30-8 ]

Yield	Reaction Conditions	Operation in experiment
72.6%	With potassium carbonate In acetonitrile Reflux;	31.A A solution of 300 mg (0.73 mmol) of methyl 4-[(4E)-3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-en-1-yl)benzoate in 30 ml of dry acetonitrile is mixed with 198.72 mg (0.87 mmol) of (5-bromopentyl)benzene and 151 mg (1.09 mmol) of anhydrous potassium carbonate and heated under reflux for 12 h. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3). 295 mg (0.53 mmol, 72.6% of theory) of an oil are obtained.1H-NMR (400 MHz, DMSO-d6, δ/ppm): 7.83 (2H, d), 7.71 (2H, d), 7.4-7.33 (2H, m), 7.29 (2H, d), 7.27-7.21 (2H, m), 7.2-7.1 (5H, m), 6.95-6.83 (2H, m), 6.44-6.35 (1H, m), 6.11-6.03 (1H, m), 3.95-3.83 (2H, m), 3.79 (3H, s), 2.91-2.79 (1H, m), 2.79-2.57 (3H, m), 2.57-2.39 (4H, m), 1.84-1.73 (1H, m), 1.72-1.5 (6H, m).LC-MS (method 1): Rt=3.57 min.MS (ESIpos): m/z=558 (M+H)+.

Reference： [1]Current Patent Assignee: BAYER AG - US2009/215843, 2009, A1 Location in patent: Page/Page column 27-28

51
[ 14469-83-1 ]
[ 502-85-2 ]
[ 1192596-44-3 ]

Yield	Reaction Conditions	Operation in experiment
3%	Stage #1: sodium 4-hydroxybutanoate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 60℃; for 1h; Stage #2: (5-bromopentyl)benzene In N,N-dimethyl-formamide; mineral oil for 504h;	52.1 Example 52; (R)-4-Dimethylamino-3-[4-(5-phenyl-pentyloxy)-butyrylamino]-butyric acid; Step 1: Sodium hydride (60% dispersion in mineral oil, 228 mg, 5.7 mmol) was added to a solution of sodium 4-hydroxybutyrate (600 mg, 4.76 mmol) in N,N-dimethylformamide (5 mL). The reaction was heated at 60° C. for 1 h, then (5-bromopentyl)-benzene (1.15 g, 5.08 mmol) was added, then after 3 weeks 1 M aq. hydrochloric acid solution was added and the reaction mixture evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced 4-(5-phenyl-pentyloxy)-butyric acid (32 mg, 3%) as a colorless oil.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2009/270505, 2009, A1 Location in patent: Page/Page column 18

52
[ 14469-83-1 ]
[ 934810-03-4 ]
[ 934810-05-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate In acetonitrile for 12h; Reflux;	19.A Example 19A Methyl 4-((3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-{2-[(5-phenylpentyl)oxy]-phenyl}but-3-en-1-yl)benzoate 273 mg (1.2 mmol) of (5-bromopentyl)benzene and 222 mg (1.6 mmol) of anhydrous potassium carbonate are added to a solution of 350 mg (0.8 mmol) of methyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 10 ml of dry acetonitrile, and the mixture is heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9:1). This gives 275 mg (58% of theory) of a solid. 1H-NMR (400 MHz, DMSO-d6, δ/ppm): 7.82 (2H, d), 7.37-7.22 (5H, m), 7.21-7.09 (4H, m), 6.91-6.80 (2H, m), 6.32 (1H, d), 6.04-5.94 (1H, m), 3.99 (2H, q), 3.89 (2H, t), 3.80 (3H, s), 2.85-2.76 (1H, m), 2.73-2.62 (1H, m), 2.59 (2H, t), 2.45-2.32 (1H, m), 2.25-2.19 (2H, m), 1.75-1.49 (5H, m), 1.45-1.32 (4H, m), 1.29-1.15 (1H, m), 1.10 (3H, t), 0.41-0.32 (2H, m), 0.31-0.23 (2H, m).

Reference： [1]Current Patent Assignee: BAYER AG - US2009/286882, 2009, A1 Location in patent: Page/Page column 17

53
[ 3612-20-2 ]
[ 14469-83-1 ]
C₂₂H₂₉NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: With iodine; magnesium Heating / reflux; Stage #2: (5-bromopentyl)benzene In tetrahydrofuran for 1h; Heating / reflux; Stage #3: 1-phenylmethyl-4-piperidone With water more than 3 stages;	15.A Part A. Preparation of Alcohol Intermediate Magnesium turnings (0.606 g, 24.95 mmol) and iodine were heated in a 3-neck flask (fitted with an addition funnel and a reflux condensor) with a heat-gun until iodine vapors appeared. After cooling to ambient temperature, tetrahydrofuran (10 mL) was added, followed by the slow addition of a solution of 1-bromo-4-n-pentylbenzene (5.00 g, 22.01 mmol) in tetrahydrofuran (50 mL). The mixture was heated with a heat-gun during the addition. After the addition was complete, the mixture was heated at reflux for 1 hr. The reaction mixture was then cooled in an ice-bath, and a solution of 1-benzyl-4-piperidone (2.78 g, 14.67 mmol) in tetrahydrofuran (40 mL) was quickly added. After slowly warming over 3 hr, the reaction mixture was re-cooled in an ice-bath. Water (25 mL) was added, followed by ethyl acetate (25 mL). The organic layer was removed, and the aqueous layer was further extracted with ethyl acetate. The organic layer was washed with saturated NaCl and dried over Na2SO4. Chromatography (on silica, ethyl acetate/hexanes) produced an alcohol in the form of a pale yellow oil (4.43 g, 90%).

Reference： [1]Current Patent Assignee: PFIZER INC - US2005/9838, 2005, A1 Location in patent: Page 131

54
[ 14469-83-1 ]
[ 934753-05-6 ]
[ 934737-87-8 ]

Yield	Reaction Conditions	Operation in experiment
99.5%	With potassium carbonate In acetonitrile for 12h; Reflux;	12A Example 12A; Methyl 4-((3E)-2-[2-(4-cyanophenyl)ethyl]-4-{2-[(5-phenylpentyl)oxy]phenyl}but-3-en-1-yl)benzoate 464.2 mg (2.04 mmol) of (5-bromopentyl)benzene and 353.05 mg (2.55 mmol) of potassium carbonate are added to a solution of 700.8 mg (1.7 mmol) of methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 65 ml of acetonitrile, and the mixture is stirred under reflux for 12 hours. After cooling, the potassium carbonate is filtered off and the filtrate is evaporated. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3). 945 mg (1.7 mmol, 99.5% yield) are obtained.LC-MS (method 2): Rt=3.37 min; MS (ESIpos): m/z=575 (M+NH4+).

Reference： [1]Current Patent Assignee: BAYER AG - US2010/29772, 2010, A1 Location in patent: Page/Page column 17-18

55
[ 14469-83-1 ]
[ 942399-47-5 ]
[ 1093172-36-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;	5-1 (5-1) Synthesis of {1,1-bis(hydroxymethyl)-3-[4-(5-phenylpentyloxy)-3-trifluoromethylphenyl]propyl}carbamic acid t-butyl ester (compound 5-1) Compound 3-6 (380 mg) was dissolved in N,N-dimethylformamide (10 ml), potassium carbonate (277 mg) and 5-phenylpentylbromide (281 mg) were added, and the mixture was stirred at 80°C for 6 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (560 mg) as a colorless oil. 1H-NMR(CDCl3) δ (ppm): 1.45(9H, s), 1.45-1.59(2H, m), 1.60-1.72(2H, m), 1.79-1.91(4H, m), 2.57-2.68(4H, m), 3.25(2H, brs), 3.63-3.68(2H, m), 3.84-3.90(2H, m), 4.00(2H, t, J=6.4Hz), 5.02(1H, brs), 6.88(1H, d, J=8.5Hz), 7.15-7.19(3H, m), 7.24-7.31(3H, m), 7.36(1H, brs).

Reference： [1]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - EP2168944, 2010, A1 Location in patent: Page/Page column 41

56
[ 14469-83-1 ]
[ 118647-85-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium azide In N,N-dimethyl-formamide at 80℃;
75%	With sodium azide In dimethyl sulfoxide
75%	With sodium azide In dimethyl sulfoxide

Reference： [1]Colombano, Giampiero; Travelli, Cristina; Galli, Ubaldina; Caldarelli, Antonio; Chini, Maria Giovanna; Canonico, Pier Luigi; Sorba, Giovanni; Bifulco, Giuseppe; Tron, Gian Cesare; Genazzani, Armando A. [Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 616 - 623]
[2]Suzuki, Takayoshi; Ota, Yosuke; Kasuya, Yuki; Mutsuga, Motoh; Kawamura, Yoko; Tsumoto, Hiroki; Nakagawa, Hidehiko; Finn; Miyata, Naoki [Angewandte Chemie - International Edition, 2010, vol. 49, # 38, p. 6817 - 6820]
[3]Suzuki, Takayoshi; Ota, Yosuke; Ri, Masaki; Bando, Masashige; Gotoh, Aogu; Itoh, Yukihiro; Tsumoto, Hiroki; Tatum, Prima R.; Mizukami, Tamio; Nakagawa, Hidehiko; Iida, Shinsuke; Ueda, Ryuzo; Shirahige, Katsuhiko; Miyata, Naoki [Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575]

57
[ 14469-83-1 ]
[ 1309380-29-7 ]
[ 1309380-30-0 ]

Yield	Reaction Conditions	Operation in experiment
52%	With triethylamine In tetrahydrofuran at 20℃; for 18h;	6 3-bromo-4-((5-phenylpentyl)thio)benzaldehyde A mixture of Intermediate 5 (0.58 g, 2.34 mmol) 1-bromo-5-phenyl pentane [14469-83-1] (0.64 g, 2.82 mmol) and triethylamine (0.65 mL, 4.66 mmol) in THF (10 mL) was stirred for 18 h at rt. After an aqueous work up with 3:1 hexanes/ethyl acetate (200 mL) the crude material was dried and concentrated onto silica gel and purified by Auto-column (9.5 hexanes: 0.5 ethyl acetate) to give 3-bromo-4-((5-phenylpentyl)thio)benzaldehyde Intermediate 7 as a pure product, 0.48 g, (52%). [0694] 1H NMR (300 MHz, CDCl3): δ 9.87 (s, 1H), 8.00 (d, J=1.5 Hz, 1H), 7.76-7.73 (m, 1H), 7.29-7.16 (series of m, 6H), 2.98 (t, J=7.2 Hz, 2H), 2.64 (t, J=7.2 Hz, 2H), 1.90-1.55 (series of m, 6H).
42%	With triethylamine In tetrahydrofuran at 20℃; for 18h;	4.2 Step-2: A solution of Intermediate 5 (2.80 g, 1 1 .3 mmol) and (5- bromopentyl)benzene [CAS 14469-83-1 ] (2.61 g, 1 1 .5 mol) with triethylamine (3.1 ml_) in THF (30 ml_) was stirred at rt for 18 hr. The solvent was removed under vacuum and the residue was dissolved in EtOAc/Hexanes (200 ml_, 1 :1 ), washed 5 with water, dried over MgSO4, filtered and concentrated onto silica gel. Auto-column (9.5 Hexanes/0.5 EtOAc) gave Intermediate 6 an oil, 1 .74 g (42%) 3-bromo-4-((5- phenylpentyl)thio)benzaldehyde.1 H NMR (300 MHz, CDCI3): δ 9.86 (s, 1 H), 7.98 (d, J = 1 .8 Hz, 1 H), 7.72 (dd, J = 8.4, 1 .2 Hz, 1 H), 7.28-7.15 (m, 6H), 2.97 (t, J = 7.5 Hz, 2H), 2.63 (t, J = 7.5 Hz, 2H), l o 1 .79-1 .54 (series of m, 6H).

Reference： [1]Current Patent Assignee: ABBVIE INC - US2014/171393, 2014, A1 Location in patent: Page/Page column 0692-0694
[2]Current Patent Assignee: ABBVIE INC - WO2011/66179, 2011, A1 Location in patent: Page/Page column 42

58
[ 14469-83-1 ]
[ 5847-59-6 ]
[ 1378872-59-3 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 18h;	2-bromo-4-nitro-1-((5-phenylpentyl)oxy)benzene A mixture of <strong>[5847-59-6]2-bromo-4-nitrophenol</strong> (CAS 5847-59-6) (2.05 g, 9.4 mmol), (5-bromopentyl)benzene (CAS 14469-83-1) (2.41 g, 10.6 mmol) and K2CO3 (3.5 g, 19.1 mmol) was dissolved in DMF (20 mL). The reaction mixture was heated at 100 C. for ~18 h. The mixture was diluted with hexanes:EtOAc (1:1) (~200 mL) and washed with H2O (3*). The organic solution was dried over MgSO4, filtered, and concentrated onto silica gel under vacuum. Auto-column (9.5 hexanes: 0.5 EtOAc) gave Intermediate 1 as a white solid 1.91 g (56%).

Reference： [1]Patent: US2012/129813,2012,A1 .Location in patent: Page/Page column 13

59
[ 14469-83-1 ]
[ 1210-83-9 ]
[ 1345995-66-5 ]

Yield	Reaction Conditions	Operation in experiment
35%	With potassium carbonate; potassium iodide In acetonitrile for 18h; Reflux; Inert atmosphere;

Reference： [1]Location in patent: experimental part Markl, Christian; Clafshenkel, William P.; Attia, Mohamed I.; Sethi, Shalini; Witt-Enderby, Paula A.; Zlotos, Darius P. [Archiv der Pharmazie, 2011, vol. 344, # 10, p. 666 - 674]

60
5-[4-(tetr-butyldimethylsilanyloxy)-3-methyl-phenylsulfanyl-methyl]-4-methyl-2-[(4-trifluoromethyl)phenyl]thiazole [ No CAS ]
[ 14469-83-1 ]
5-[1-[3-methyl-4-(tert-butyldimethylsilyloxy)phenylthio]-6-phenylhexyl]-2-[4-(trifluoromethyl)phenyl]-4-methylthiazol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5-[4-(tetr-butyldimethylsilanyloxy)-3-methyl-phenylsulfanyl-methyl]-4-methyl-2-[(4-trifluoromethyl)phenyl]thiazole With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: (5-bromopentyl)benzene In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;	4.4. 5-(1-(4-(tert-butyldimethylsilyloxy)-3-methylphenylthio)-2-phenylethyl)-4-methyl-2-(4-(trifluoromethyl)phenyl)thiazole, compound 7a General procedure: A stirred solution of 6 (300 mg, 0.59 mmol) in anhydrous THF (5 ml) was cooled to -78 °C in dryice-acetone bath under N2 atmosphere. 2.0 M lithiumdiisopropylamide (619 μl, 1.24 mmol) was added dropwise to reaction mixture at -78 °C. The reaction mixture was stirred at -78 °C for 30 min. A solution of benzyl bromide (77 μl, 0.65 mmol) in THF (1 ml) was added dropwise at -78 °C. After the mixture was stirred at same temperature for further 30 min, it was quenched by adding sat. NH4Cl solution. The mixture was diluted by ethyl acetate and the organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure to give crude compound. The crude compound was purified by column chromatography on silica gel (n-hexnane/ethylacetate = 10/1) to obtain 7a as colorless oil (265 mg, 75%).

Reference： [1]Location in patent: experimental part Ham, Jungyeob; Hwang, Hoosang; Kim, Euno; Kim, Jeong-Ah; Cho, Sung Jin; Ko, Jaeyoung; Lee, Woojin; Lee, Jaehwan; Holla, Harish; Banerjee, Joydeep; Kim, Seokho; Yang, Inho; Lee, Hyun Joo; Shin, Kyoungjin; Choi, Hyukjae; Nam, Sang-Jip; Tak, Jungae; Hahn, Dongyup; Oh, Taekyung; Won, Dong Hwan; Lee, Tae Gu; Choi, Jihye; Park, Mi Sun; Seok, Chaok; Chin, Jungwook; Kang, Heonjoong [European Journal of Medicinal Chemistry, 2012, vol. 53, p. 190 - 202]

61
[ 14469-83-1 ]
[ 100-52-7 ]
[ 1086221-41-1 ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: (5-bromopentyl)benzene With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 2.5h; Inert atmosphere; Stage #2: benzaldehyde In tetrahydrofuran at 20℃; for 2.7h; Inert atmosphere; Cooling with ice; Stage #3: With water; ammonium chloride In tetrahydrofuran Inert atmosphere;

Reference： [1]Ema, Tadashi; Nakano, Yasuko; Yoshida, Daiki; Kamata, Shusuke; Sakai, Takashi [Organic and Biomolecular Chemistry, 2012, vol. 10, # 31, p. 6299 - 6308]

62
[ 14469-83-1 ]
di(tetra-n-butylammonium)ethylzinc tribromide [ No CAS ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) In tetrahydrofuran for 2.16667h; Inert atmosphere;

Reference： [1]McCann, Lucas C.; Hunter, Howard N.; Clyburne, Jason A. C.; Organ, Michael G. [Angewandte Chemie - International Edition, 2012, vol. 51, # 28, p. 7024 - 7027]

63
[ 10521-91-2 ]
[ 141-78-6 ]
[ 14469-83-1 ]
[ 75553-28-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 52% 2: 20%	With tetrabutylammomium bromide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate In dichloromethane at 21℃; Inert atmosphere;

Reference： [1]Pouliot, Marie-France; Mahe, Olivier; Hamel, Jean-Denys; Desroches, Justine; Paquin, Jean-Francois [Organic Letters, 2012, vol. 14, # 21, p. 5428 - 5431,4]

64
[ 14469-83-1 ]
[ 1383806-71-0 ]
[ 1383806-47-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate In acetonitrile at 20℃; for 24h;

Reference： [1]Staszewski, Marek; Walczynski, Krzysztof [Medicinal Chemistry Research, 2013, vol. 22, # 3, p. 1287 - 1304]

65
[ 14469-83-1 ]
[ 1430423-77-0 ]

Yield	Reaction Conditions	Operation in experiment
51%	With N,N-dihydroxypyromellitimide; Selectfluor In acetonitrile at 50℃; for 6h; Inert atmosphere;

Reference： [1]Amaoka, Yuuki; Nagatomo, Masanori; Inoue, Masayuki [Organic Letters, 2013, vol. 15, # 9, p. 2160 - 2163]

66
[ 14469-83-1 ]
[ 140-29-4 ]
[ 1431331-63-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium amide In toluene at 80℃; for 17h;
	Stage #1: phenylacetonitrile With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: (5-bromopentyl)benzene In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	5.1.10 General procedure for preparing compounds 30 General procedure: Phenylacetonitrile (11mmol) was added dropwise to a suspension solution of NaH (11mmol) in anhydrous DMF (20mL) at 0°C under nitrogen. After the reaction mixture was stirred for 30min at rt, bromide (10mmol) was added in a dropwise manner. The resultant solution was stirred overnight at rt before water was added to quench the reaction. After the mixture was extracted with ethyl acetate, the organic phase was washed with brine, and dried over Na2SO4. Evaporation and column chromatography on silica gel afforded the crude alkylation product, which was dissolved in anhydrous Et2O. The resultant solution was added dropwise to a suspension of LiAlH4 (4.4mmol) in anhydrous Et2O at rt under nitrogen. After being stirred for 1h, the reaction was quenched by adding water. Ether extract work up followed by chromatography provided crude amine, which was dissolved in THF. To this solution were added 11b and TEA before it was refluxed for 24h. Ethyl acetate work up followed by purification by flash chromatography (eluent: 5-10% EtOH-DCM or similar conditions) gave the corresponding condensation product.

Reference： [1]Mori, Mattia; Vignaroli, Giulia; Cau, Ylenia; Dinic̈, Jelena; Hill, Richard; Rossi, Matteo; Colecchia, David; Pešic̈, Milica; Link, Wolfgang; Chiariello, Mario; Ottmann, Christian; Botta, Maurizio [ChemMedChem, 2014, vol. 9, # 5, p. 973 - 983]
[2]Zhang, Pengtao; Yang, Xinye; Zhang, Feiran; Gabelli, Sandra B.; Wang, Renxiao; Zhang, Yihua; Bhat, Shridhar; Chen, Xiaochun; Furlani, Manuel; Amzel, L. Mario; Liu, Jun O.; Ma, Dawei [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 9, p. 2600 - 2617]

67
[ 14469-83-1 ]
[ 494199-22-3 ]
[ 1433190-45-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 4-(2,5-dimethoxyphenyl)-1-methyl-1,2,3,6-tetrahydropyridine With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 2h; Inert atmosphere; Stage #2: (5-bromopentyl)benzene In tetrahydrofuran; hexane at -20 - 20℃; for 1h; Inert atmosphere;	5.1.1 General procedure A General procedure: A solution of 4 in dry THF was stirred under argon at -20 °C. A solution of n-butyllithium, 2.5 M in hexane (1.5 equiv), was added to the reaction, producing a deep red color. The mixture was stirred at -20 °C for 2 h. Alkyl bromide (1.5 equiv) was added, producing a yellow solution, which was then stirred and brought to 20 °C over 1 h. The reaction mixture was then treated with saturated NH4Cl solution. The reaction mixture was partitioned between Et2O and H2O. The organic layer was dried over anhyd Na2SO4 and removal of the solvent gave an orange oil. Column chromatography of the crude material using 20% hexanes in Et2O gave compound 5 as a pure yellow oil.
	With n-butyllithium at -78 - 20℃;

Reference： [1]Iyer, Malliga R.; Rothman, Richard B.; Dersch, Christina M.; Jacobson, Arthur E.; Rice, Kenner C. [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 3298 - 3309]
[2]Iyer, Malliga R.; Rothman, Richard B.; Dersch, Christina M.; Jacobson, Arthur E.; Rice, Kenner C. [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 531 - 539]

68
[ 14469-83-1 ]
[ 53429-15-5 ]

Yield	Reaction Conditions	Operation in experiment
90 mg	Stage #1: (5-bromopentyl)benzene With potassium phtalimide In N,N-dimethyl-formamide at 60℃; for 1h; Stage #2: With hydrazine hydrate In ethanol at 70℃; for 5h; Stage #3: With hydrogenchloride In 1,4-dioxane	96 <Example 96> - Synthesis of Compound 0096 - (Synthesis of Compound 0096-1) N,N-dimethylformamide (2 mL) was added to (5-bromopentyl)benzene (227 mg) and phthalimidepotassium (195 mg), and the mixture was stirred at 60°C for 1 hour. The reaction solution was cooled to room temperature and subjected to liquid separation with ethyl acetate (4 mL) and water (4 mL). The organic layer was washed with brine and dried over sodium sulfate, and then the solvent was evaporated under reduced pressure. A solution of the obtained oily substance and hydrazine monohydrate (100 µL) in ethanol (5 mL) was stirred at 70°C for 5 hours. The reaction solution was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was subjected to liquid separation by the addition of ethyl acetate (4 mL) and water (2 mL), and the aqueous layer was extracted with ethyl acetate (2 mL) twice. The organic layer was washed with brine and dried over sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol, NH silica) and to the obtained oily substance was added a 4 M hydrogen chloride/1,4-dioxane solution (1 mL), and the solvent was evaporated under reduced pressure. To the residue, methanol (1 mL) and ethyl acetate (1 mL) were added, and the resulting solid was separated by filtration and washed with ethyl acetate. The solid was dried under reduced pressure to obtain a compound 0096-1 hydrochloride (90 mg) as a white solid. 1H-NMR (DMSO-d6) δ: 7.83 (3H, bs), 7.30-7.26 (2H, m), 7.21-7.15 (3H, m), 2.75 (2H, dt), 2.57 (2H, t), 1.61-1.54 (4H, m), 1.37-1.27 (2H, m). MS m/z (M+H): 164.
	Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C 2.1: hydrazine hydrate / ethanol / 3 h / 78 °C 2.2: Gabriel Amine Synthesis
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C 2: hydrazine hydrate / ethanol / 3 h / Reflux

Reference： [1]Current Patent Assignee: FUJIFILM HOLDINGS CORP. - EP2727920, 2014, A1 Location in patent: Paragraph 0497-0498
[2]Bach, Anders; Pizzirani, Daniela; Realini, Natalia; Vozella, Valentina; Russo, Debora; Penna, Ilaria; Melzig, Laurin; Scarpelli, Rita; Piomelli, Daniele [Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9258 - 9272]
[3]Current Patent Assignee: ISTITUTO ITALIANO DI TECNOLOGIA; UNIVERSITY OF CALIFORNIA - WO2015/173169, 2015, A1

69
[ 616-45-5 ]
[ 14469-83-1 ]
[ 205822-31-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 2-pyrrolidinon With sodium hydride In toluene; paraffin oil for 10h; Inert atmosphere; Reflux; Stage #2: (5-bromopentyl)benzene In 5,5-dimethyl-1,3-cyclohexadiene; toluene; paraffin oil for 4h; Inert atmosphere; Reflux;	1-(4-Phenylbutyl)pyrrolidin-2-one (1c) General procedure: To a solution of pyrrolidin-2-one (3 mL; 40 mmol) in 80 mL of anhydrous toluene, was added NaH (0.95 g, 40 mmol.) in 60% suspension in paraffin oil (1.58 g suspension). After stopping of hydrogen release, the reaction mixture was heated to reflux with stirring under nitrogen atmosphere for 10 h. Then ω-phenylalkylbromide (80 mmol) dissolved in anhydrous xylene (20 mL) was added. The mixture was then refluxed for 4 h under nitrogen atmosphere. After cooling and filtration, solvent was eliminated under reduced pressure. The viscous residue was purified by flash chromatography using CH2Cl2 / MeOH (99/1) to give compound 1c

Reference： [1]Fante, Bamba; Soro, Yaya; Siaka, Sorho; Marrot, Jerome; Coustard, Jean-Marie [Synthetic Communications, 2014, vol. 44, # 16, p. 2377 - 2385]

70
[ 14469-83-1 ]
[ 1617540-53-0 ]
7-methoxy-N-{2-[4-(5-phenylpentyl)piperazin-1-yl]ethyl}-1,2,3,4-tetrahydroacridin-9-amine trihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (5-bromopentyl)benzene; 7-methoxy-N-(2-(piperazin-1-yl)ethyl)-1,2,3,4-tetrahydroacridin-9-amine With N-ethyl-N,N-diisopropylamine In dichloromethane Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In methanol	General procedure for synthesis of novel 7-MEOTA-donepezil like compounds (4-25) General procedure: General procedure for synthesis of novel 7-MEOTA-donepezil like compounds (4-25) Intermediate 3 (0.2 g, 0.6 mmol) was dissolved in anhydrous CH2Cl2 and Hunig's base (0.45 g, 3.6 mmol) with appropriate alkylbromide (1.8 mmol) was added. The reaction mixture was refluxed under nitrogen atmosphere overnight followed by evaporation of volatile solvents under reduced pressure. The crude product was purified by flash chromatography eluting EtOAc/MeOH/NH3 (25% aq.) (40:1:0.2-15:1:0.2) to obtain yellow-to-white oily residue. Resulting free bases were dissolved in methanol and gassed with hydrochloride acid to obtain final products as yellow-to-white salts in 65-85% yields.

Reference： [1]Korabecny, Jan; Dolezal, Rafael; Cabelova, Pavla; Horova, Anna; Hruba, Eva; Ricny, Jan; Sedlacek, Lukas; Nepovimova, Eugenie; Spilovska, Katarina; Andrs, Martin; Musilek, Kamil; Opletalova, Veronika; Sepsova, Vendula; Ripova, Daniela; Kuca, Kamil [European Journal of Medicinal Chemistry, 2014, vol. 82, p. 426 - 438]

71
[ 14469-83-1 ]
[ 4244-84-2 ]
ethyl N-(5-phenylpentyl)-β-alaninate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
480 mg	Stage #1: ethyl β-alaninate hydrochloride With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: (5-bromopentyl)benzene In N,N-dimethyl-formamide; mineral oil at 80℃; for 4h;	C-1 Ethyl N-(5-phenylpentyl)-β-alaninate Reference Example C-1 Ethyl N-(5-phenylpentyl)-β-alaninate To a solution of β-alanine ethyl hydrochloride (2.00 g) in N,N-dimethylformamide (65.0 mL), sodium hydride (60% dispersion in mineral oil, 1.15g) was added and the mixture was stirred at room temperature for an hour. After adding (5-bromopentyl)benzene (2.52 mL), the mixture was stirred at 80°C for 4 hours. After being cooled to room temperature, the reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic layer was separated off and dried over anhydrous magnesium sulfate; after removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol = 100:0-85:15) to give the titled compound as a pale yellow oil (480 mg). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.19 - 1.30 (m, 3 H) 1.31 - 1.70 (m, 6 H) 2.42 - 2.54 (m, 2 H) 2.56 - 2.67 (m, 4 H) 2.81 - 2.92 (m, 2 H) 4.14 (q, J=7.1 Hz, 2 H) 7.10-7.22 (m, 3 H) 7.23 - 7.32 (m, 2 H). MS ESI/APCI Dual posi: 264[M+H]+.

Reference： [1]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD. - EP2881384, 2015, A1 Location in patent: Paragraph 0567; 0568

72
[ 14469-83-1 ]
[ 65700-72-3 ]
(4S,4aR,7aS,12bR)-4a,9-dihydroxy-3-(5-phenylpentyl)-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]-isoquinolin-7(7aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃;

Reference： [1]Selfridge, Brandon R.; Wang, Xiaohui; Zhang, Yingning; Yin, Hang; Grace, Peter M.; Watkins, Linda R.; Jacobson, Arthur E.; Rice, Kenner C. [Journal of Medicinal Chemistry, 2015, vol. 58, # 12, p. 5038 - 5052]

73
[ 14469-83-1 ]
[ 1258959-98-6 ]
4-((5-phenylpentyl)oxy)benzofuran-7-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
604 mg	With potassium carbonate In dimethyl sulfoxide at 20℃; for 16h;	3 Intermediate 74-((5-ihenylientyl)oxy)benzofuran-7-carbonitrile To the solution of intermediate 4 (427mg, 2.68mmol) and 5-bromopentyl) benzene (914mg, 4.O2mmol) (CAS 14469-83-1) in DMSO (1 0mL) was added K2C03 (1 .48g, I 0.7mmol). After stirring at rt for 16 h the mixture was diluted with water, extracted with ethyl acetate. The organic layers were combined, washed with brine,dried over magnesium sulfate, and concentrated under reduced pressure. The crude material was purified by MPLC (10% ethyl acetate in hexanes)to afford 604mg of Intermediate 7 as colorless solid.1H NMR (600 MHz, CDCI3) 6: 7.64 (d, J2.05 Hz, I H), 7.53 (d, J8.50 Hz, IH), 7.27-7.31 (m, 2H), 7.15-7.22 (m, 3H), 6.90 (d, J=2.05 Hz, IH), 6.69 (s, IH), 4.15(s, 2H), 2.61-2.72 (m, 2H), 1.82-2.04 (m, 2H), 1.65-1.79 (m, 2H), 1.45-1.62 (m, 2H).

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2015/163936, 2015, A1 Location in patent: Page/Page column 28; 29

74
[ 14469-83-1 ]
8-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)quinolin-5-ol [ No CAS ]
5-((5-phenylpentyl)oxy)-8-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
506 mg	With potassium carbonate In dimethyl sulfoxide at 20℃; for 16h;	11 5-((5-phenylpentyl)oxy)-8-(((tetrahydro-2H-pyran-2-yI)oxy)methyl)gu inoline To the solution of intermediate 20 (440mg, 1 .7mmol) and (5- bromopentyl)benzene (579mg, 2.SSmmol) (CAS 14469-83-I) in DMSO (I5mL) was added K2C03 (938g, 6.8mmol). After stirring at rt for 16 h the mixture was diluted with water, extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude material was purified by MPLC (30% ethyl acetate in hexanes) to afford 506mgof Intermediate 21 as colorless solid.1H NMR (600 MHz, CDCI3) 6: 8.87-8.99 (m, I H), 8.50-8.62 (m, I H), 7.65-7.78 (m, IH), 7.34-7.41 (m, IH), 7.24-7.32 (m, 2H), 7.15-7.23 (m, 3H), 6.80-6.85 (m,IH), 5.30-5.40 (m, IH), 5.15-5.26 (m, IH), 4.83-4.91 (m, IH), 4.06-4.19 (m, 2H), 3.93-4.05 (m, I H), 3.50-3.64 (m, I H), 2.62-2.74 (m, 2H), 1.88-2.02 (m, 3H), 1.68-1.85 (m,4H), 1 .48-1 .66 (m, 5H)

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2015/163936, 2015, A1 Location in patent: Page/Page column 38; 39

75
[ 136918-14-4 ]
[ 14469-83-1 ]
[ 53429-14-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;	Intermediate 14. 2-(5-phenyl pentyl)isoindoline-1,3-dione General procedure: XII (1.0 eq.) and phthalimide (1.0 eq.) were dissolved in dry DMF (2.0 mL per mmcl Xli) andK2C03 (1.0 eq.) was added. The reaction mixture was stirred at rt for 15 h, then diluted with EtOAc(5.0 mL per mmol XII) and filtered. The filtrate was evaporated under reduced pressure and the crude was used in the following step without further purification. The title compound was obtained according to the General Procedure VI (Step ib), starting from (5-bromopentyl)benzene (1.54 g, 6.79 mmcl) and phthalimide (1.0 g, 6.79 mmol). White solid (1.73 g, 87%). ‘H NMR (400 MHz, DMSO-d6) 6 1.21 - 1.34 (m, 2H), 1.49 - 1.69 (m, 4H), 2.52 - 2.56 (m, 1H), 3.55 (t, J = 7.1 Hz, 2H), 7.08 - 7.17 (m, 3H), 7.17 - 7.28 (m, 2H), 7.79 - 7.91 (m, 4H). MS (ESI) m/z: 294 [M-H] 311 [M-NH4]. MS (ESI) m/z: 292 [M-H].
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere;	Intermediate 62. 2-(5-Phenylpentyl)isoindoline-l,3-dione Intermediate 62. 2-(5-Phenylpentyl)isoindoline-l,3-dione In an oven-dried flask, phthalimide (736 mg, 5.0 mmol), 5-bromopentylbenzene (1.14 g, 5.0 mmol) and K2CO3 (691 mg, 5.0 mmol) were dissolved in dry DM F (10 mL) and the solution was stirred under nitrogen at room temperature for 15 hours. EtOAc (20 mL) was added, the precipitate was filtered off and the filtrate was evaporated leaving the crude product which was used in the following step without further purification.
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;

Reference： [1]Current Patent Assignee: ISTITUTO ITALIANO DI TECNOLOGIA; UNIVERSITY OF CALIFORNIA - WO2015/173169, 2015, A1 Location in patent: Paragraph 19; 39; 45; 46
[2]Current Patent Assignee: UNIVERSITY OF CALIFORNIA; ISTITUTO ITALIANO DI TECNOLOGIA - WO2015/173168, 2015, A1 Location in patent: Page/Page column 63
[3]Bach, Anders; Pizzirani, Daniela; Realini, Natalia; Vozella, Valentina; Russo, Debora; Penna, Ilaria; Melzig, Laurin; Scarpelli, Rita; Piomelli, Daniele [Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9258 - 9272]

76
[ 14469-83-1 ]
[ 123770-62-7 ]
ethyl 5-(5-phenylpentyloxymethyl)isoxazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.65 g		Reference Production Example 109 (0751) 60% Sodium hydride (1.04 g, 26.0 mmol) was added to dehydrated N,N-dimethylformamide (10 ml) cooled to 0C, under a nitrogen atmosphere, and a dehydrated N,N-dimethylformamide (10 ml) solution of <strong>[123770-62-7]ethyl 5-hydroxymethylisoxazole-3-carboxylate</strong> (3.0 g, 17.54 mmol) was added dropwise thereto, and then the mixture was further stirred for 30 minutes. A dehydrated N,N-dimethylformamide (5 ml) solution of 1-bromo-5-phenylpentane (3.90 g, 17.54 mmol) was added thereto, and the mixture was heated to room temperature and stirred for 16 hours. Then, the mixture was added to a saturated aqueous ammonium chloride solution, and extracted twice with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 1.65 g of ethyl 5-(5-phenylpentyloxymethyl)isoxazole-3-carboxylate represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 7.29 (m, 2H), 7.17(m, 3H), 6.65(s, 1H), 4.61 (s, 2H), 4.44 (t, 2H), 3.51(t, 2H), 2.61 (t, 2H), 1.62 (m, 4H), 1.42 (t, 5H)

Reference： [1]Patent: EP2952096,2015,A1 .Location in patent: Paragraph 0751

77
[ 4224-70-8 ]
[ 1078-58-6 ]
[ 14469-83-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 6-bromohexanoic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; Stage #2: diphenylzinc With iron(III)-acetylacetonate; o-phenylenebis(diphenylphosphine) In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;

Reference： [1]Toriyama, Fumihiko; Cornella, Josep; Wimmer, Laurin; Chen, Tie-Gen; Dixon, Darryl D.; Creech, Gardner; Baran, Phil S. [Journal of the American Chemical Society, 2016, vol. 138, # 35, p. 11132 - 11135]

78
4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl 6-bromohexanoate [ No CAS ]
[ 1078-58-6 ]
[ 14469-83-1 ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: 4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl 6-bromohexanoate; diphenylzinc With iron(III)-acetylacetonate; o-phenylenebis(diphenylphosphine) In tetrahydrofuran at 0 - 25℃; for 1h; Inert atmosphere; Stage #2: Inert atmosphere;

Reference： [1]Toriyama, Fumihiko; Cornella, Josep; Wimmer, Laurin; Chen, Tie-Gen; Dixon, Darryl D.; Creech, Gardner; Baran, Phil S. [Journal of the American Chemical Society, 2016, vol. 138, # 35, p. 11132 - 11135]

79
[ 14469-83-1 ]
[ 64-04-0 ]
N-(5-phenylpentyl)-N-(2-phenylethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 8h;	5 6.1.1.5 N-phenethyl-5-phenylpentan-1-amine (5) To a solution of phenethylamine 34 (0.8mmol) in DMF (5mL), K2CO3 (1.00mmol) was added. To this reaction mixture, (5-bromopentyl)benzene 39 (0.8mmol) and KI (0.2mmol) were added and heated at 60°C for 8h. After the completion of the reaction, water was added to the mixture and extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography. Yield 75%, Colorless oil, Rf 0.25 (1: 9 MeOH: CH2Cl2), IR (neat): 3373, 2945, 1515, 1211, 967, 868cm-1; 1H NMR (CDCl3) δ 1.29-1.37 (m, 2H), 1.49-1.56 (m, 2H), 1.57-1.65 (m, 2H), 2.02 (bs, 1H), 2.57-2.65 (m, 4H), 2.79-2.91 (m, 4H), 7.15-7.31 (m, 10H); 13C NMR (CDCl3) δ 26.98, 29.70, 31.36, 35.89, 36.16, 49.72, 51.15, 125.79, 126.34, 128.41, 128.55, 128.64, 128.87, 140.07, 142.79. HRMS Calcd for C19H25Nm/z [M+H] 268.2066, found 268.2095.

Reference： [1]Manickam, Manoj; Jalani, Hitesh B.; Pillaiyar, Thanigaimalai; Sharma, Niti; Boggu, Pulla Reddy; Venkateswararao, Eeda; Lee, You-Jung; Jeon, Eun-Seok; Jung, Sang-Hun [European Journal of Medicinal Chemistry, 2017, vol. 134, p. 379 - 391]

80
[ 14469-83-1 ]
[ 23095-14-9 ]
[ 2098885-65-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere;

Reference： [1]Kornahrens, Anne F.; Cognetta, Armand B.; Brody, Daniel M.; Matthews, Megan L.; Cravatt, Benjamin F.; Boger, Dale L. [Journal of the American Chemical Society, 2017, vol. 139, # 20, p. 7052 - 7061]

81
[ 104-92-7 ]
[ 14469-83-1 ]
1-methoxy-4-(1-phenylpentyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 1-bromo-4-methoxy-benzene; (5-bromopentyl)benzene With manganese; 6,6'-dimethyl-2,2'-bipyridine; nickel(II) perchlorate hexahydrate In N,N-dimethyl acetamide at 25℃; for 8h; Inert atmosphere; Sealed tube; Stage #2: With propyl bromide In N,N-dimethyl acetamide at 25℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;

Reference： [1]Chen, Fenglin; Chen, Ke; Zhang, Yao; He, Yuli; Wang, Yi-Ming; Zhu, Shaolin [Journal of the American Chemical Society, 2017, vol. 139, # 39, p. 13929 - 13935]

82
[ 101-55-3 ]
[ 14469-83-1 ]
C₂₃H₂₄O [ No CAS ]
C₂₃H₂₄O [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 310 - 313

83
[ 108-86-1 ]
[ 14469-83-1 ]
[ 1726-12-1 ]

Yield	Reaction Conditions	Operation in experiment
	With nickel(II) bromide dimethoxyethane; Ir[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine]₂(1,10-phenantroline)PF₆; Bathocuproine; diisopropylamine; magnesium bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; Irradiation; regioselective reaction;

Reference： [1]Peng, Long; Li, Zheqi; Yin, Guoyin [Organic Letters, 2018, vol. 20, # 7, p. 1880 - 1883]

84
[ 14469-83-1 ]
2-(pyrimidin-5-yl)phenol [ No CAS ]
5-(2-((5-phenylpentyl)oxy)phenyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In acetone at 70℃; for 24h; Inert atmosphere; Sealed tube;
80%	With potassium carbonate In acetone at 70℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;

Reference： [1]Jayarajan, Ramasamy; Das, Jayabrata; Bag, Sukdev; Chowdhury, Rajdip; Maiti, Debabrata [Angewandte Chemie - International Edition, 2018, vol. 57, # 26, p. 7659 - 7663][Angew. Chem., 2018, vol. 130, # 26, p. 7785 - 7789,5]
[2]Brochetta, Massimo; Borsari, Tania; Bag, Sukdev; Jana, Sadhan; Maiti, Siddhartha; Porta, Alessio; Werz, Daniel B.; Zanoni, Giuseppe; Maiti, Debabrata [Chemistry - A European Journal, 2019, vol. 25, # 44, p. 10323 - 10327]

85
5-isobutyl-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione [ No CAS ]
[ 14469-83-1 ]
5-isobutyl-1,3-dimethyl-5-(5-phenylpentyl)pyrimidine-2,4,6(1H,3H,5H)-trione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere;

Reference： [1]Huang, Huan-Ming; Procter, David J. [European Journal of Organic Chemistry, 2019, vol. 2019, # 2, p. 313 - 317]

86
[ 111-24-0 ]
[ 108-86-1 ]
[ 14469-83-1 ]

Yield	Reaction Conditions	Operation in experiment
0.94 kg	Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran for 3.5h; Inert atmosphere; Large scale; Stage #2: 1,5-dibromo-pentane In tetrahydrofuran at 10 - 45℃; Inert atmosphere; Large scale;	Synthesis of Intermediate 1 Milled magnesium (190 g) under nitrogen in a 10 L reactor,Activated with dry THF (0.3 L), a small amount of iodine,Solution of bromobenzene (1192 g) in dry THF (3.5 L)Drip into the solution over 2 hours,The mixture was stirred for 1.5 hours under reflux to prepare a Grignard reagent solution.In a 20 L reactor,1,5-dibromopentane (4365 g) dry THF under nitrogenAdd (5.2 L) and add the previously prepared catalyst solution,After cooling to an internal temperature of 10 ° C., the previously prepared Grignard reagent solution isAs the internal temperature is 10-45 ° C,After dripping over 1 hour, it stirred at room temperature overnight.Add 3 M hydrochloric acid (3.5 L), separate the oil layer,The aqueous layer was further extracted with ethyl acetate (3.5 × 2).After drying the oil layer with anhydrous magnesium sulfate and filtering the oil layer,The filtrate was concentrated to give a crude brown oily substance (4.9 kg).The crude product is distilled under reduced pressure to give Intermediate 1 as a pale yellow clear oil.(0.94 kg) was obtained.

Reference： [1]Current Patent Assignee: Mitsubishi Chemical Corp (in: MCHC Group); MITSUBISHI CHEMICAL HOLDINGS CORPORATION - JP2019/38775, 2019, A Location in patent: Paragraph 0070; 0071

87
[ 14469-83-1 ]
[ 6952-59-6 ]
[ 1087-49-6 ]

Yield	Reaction Conditions	Operation in experiment
0.45 kg	Stage #1: (5-bromopentyl)benzene With iodine; magnesium In tetrahydrofuran at 55℃; for 2h; Inert atmosphere; Large scale; Stage #2: 3-cyanobromobenzene In tetrahydrofuran at 10 - 58℃; for 3.75h; Large scale; Stage #3: With hydrazine hydrate; sodium hydroxide In diethylene glycol dimethyl ether at 80 - 123℃; for 5.5h; Large scale;	Synthesis of Intermediate 2 Milled magnesium (107 g) under nitrogen in a 10 L reactor,Add dry THF (0.5 L), activate with iodine fragments (tens of mg),A solution of intermediate 6 (0.91 kg) in dry THF (2.5 L) was added dropwise over 2 hours,The solution was heated and stirred at an internal temperature of 55 ° C. for one hour to prepare a Grignard reagent solution. After cooling 3-bromobenzonitrile and dry THF (4.5 L) to 10 ° C., the Grignard reagent solution prepared above wasAdd dropwise over 45 minutes at an internal temperature of 10 to 35 ° C,The mixture was heated and stirred at an internal temperature of 45 to 58 ° C. for 3 hours.The above reaction solution was added dropwise to 3 M hydrochloric acid (4.3 L), cooled to room temperature, the oil layer was separated, and the aqueous layer was extracted with ethyl acetate (6 L).Combine the oil layers and dry over anhydrous magnesium sulfate,After filtering the oil layer, the filtrate is concentrated,A brown oily crude (2.0 kg) was obtained.The crude product is purified by silica gel column chromatography (ethyl acetate / hexane = 1 / 9-1 / 4) to give a pale yellow transparent oil(0.74 kg) was obtained.Then transfer to a 20 L reactor and charge diglyme (5.1 L),Sodium hydroxide (0.19 kg) was added. ThenAdd hydrazine monohydrate (0.24 kg) dropwise over 30 minutes,Raise the internal temperature to 80 ° C over 1 hour,The mixture was stirred at an internal temperature of 123 ° C. for 4 hours. After coolingAfter adding 2 M hydrochloric acid (3.6 L),Hexane (3.5 L) was added and the oil layer separated.The aqueous layer is extracted with hexane (2.5 L × 2 times),Combine the oil layers and wash with saturated saline (2.5 L),After drying over anhydrous magnesium sulfate and filtering the oil layer,The filtrate was concentrated to give a crude brown oil (0.92 kg).The crude product was purified by silica gel column chromatography (hexane) to give Intermediate 2 (0.45 kg) as a yellow clear oil.

Reference： [1]Current Patent Assignee: Mitsubishi Chemical Corp (in: MCHC Group); MITSUBISHI CHEMICAL HOLDINGS CORPORATION - JP2019/38775, 2019, A Location in patent: Paragraph 0072; 0073; 0074

88
[ 14469-83-1 ]
[ 5281-18-5 ]
[ 1087-49-6 ]

Yield	Reaction Conditions	Operation in experiment
51%	With tetrakis(pyridine)nickel dichloride; potassium <i>tert</i>-butylate; triphenylphosphine In 1,4-dioxane at 60℃; for 24h; Schlenk technique; Inert atmosphere;
51%	With nickel(II) bromide dimethoxyethane; lithium tert-butoxide; trimethylphosphane In 1,4-dioxane at 60℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Zhu, Dianhu; Lv, Leiyang; Qiu, Zihang; Li, Chao-Jun [Journal of Organic Chemistry, 2019]
[2]Zhu, Dianhu; Lv, Leiyang; Qiu, Zihang; Li, Chao-Jun [Journal of Organic Chemistry, 2019, vol. 84, # 10, p. 6312 - 6322]

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CAS No. :	14469-83-1	MDL No. :	MFCD01075177
Formula :	C₁₁H₁₅Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QICUPOFVENZWSC-UHFFFAOYSA-N
M.W :	227.14	Pubchem ID :	285561
Synonyms :

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.45
Num. rotatable bonds :	5
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	58.51
TPSA :	0.0 Å²

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.07 cm/s

Log Po/w (iLOGP) :	2.85
Log Po/w (XLOGP3) :	0.86
Log Po/w (WLOGP) :	3.79
Log Po/w (MLOGP) :	4.27
Log Po/w (SILICOS-IT) :	4.21
Consensus Log Po/w :	3.2

[ CAS No. 14469-83-1 ] {[proInfo.proName]}

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Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.83
Solubility :	3.36 mg/ml ; 0.0148 mol/l
Class :	Very soluble
Log S (Ali) :	-0.44
Solubility :	81.8 mg/ml ; 0.36 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-5.28
Solubility :	0.00119 mg/ml ; 0.00000525 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
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P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
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P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
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P331	Do NOT induce vomiting.
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P335	Brush off loose particles from skin.
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P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
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P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 14469-83-1 ] {[proInfo.proName]}

Quality Control of [ 14469-83-1 ]

Related Doc. of [ 14469-83-1 ]

Product Details of [ 14469-83-1 ]

Calculated chemistry of [ 14469-83-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 14469-83-1 ]

Application In Synthesis of [ 14469-83-1 ]

[ 14469-83-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 14469-83-1 ]

Aryls

Bromides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 14469-83-1 ]