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[ CAS No. 4383-22-6 ]

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Chemical Structure| 4383-22-6
Chemical Structure| 4383-22-6
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CAS No. :4383-22-6MDL No. :MFCD00463446
Formula : C10H13N Boiling Point : 217.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :147.22Pubchem ID :-
Synonyms :

Computed Properties of [ 4383-22-6 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 4383-22-6 ]

Signal Word:DangerClass:8
Precautionary Statements:P280-P305+P351+P338-P310UN#:3267
Hazard Statements:H314Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4383-22-6 ]

  • Downstream synthetic route of [ 4383-22-6 ]

[ 4383-22-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 100-39-0 ]
  • [ 107-11-9 ]
  • [ 4383-22-6 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate at 20℃; for 24h;
92% for 16h; Ambient temperature;
91% With potassium carbonate at 20℃; for 3.5h; Inert atmosphere;
90% With potassium carbonate at 20℃; for 24h; Inert atmosphere;
88% With potassium carbonate at 25℃; for 3h; Inert atmosphere;
78% for 48h; Heating;
78% at 0 - 20℃; for 16h; Inert atmosphere;
76% With potassium carbonate at 20℃; for 3h; 1 Synthesis of N-benzylprop-2-en-1-amine (Bromomethyl)benzene (0.992 mL, 8.35 mmol) was gradually added dropwise to a suspension of anhydrous potassium carbonate (1.39 g, 10.0 mmol) and prop-2-en-1-amine (7.53 mL, 100 mmol) and then stirred for 3 hours at room temperature. The solids were filtered and washed with methylene chloride. The combined organic layer was evaporated under reduced pressure. The resulting residue was purified with CHROMATOREX Q-PACK SI30 SIZE 20 (hexane: ethyl acetate = 50%:50% to 0%:100%) to obtain the aforementioned compound (934 mg, yield: 76%).
76% With potassium carbonate at 20℃; for 3h; 1 Synthesis of N-benzylprop-2-en-1-amine (Bromomethyl)benzene (0.992 mL, 8.35 mmol) was gradually added dropwise to a suspension of anhydrous potassium carbonate (1.39 g, 10.0 mmol) and prop-2-en-1-amine (7.53 mL, 100 mmol) and then stirred for 3 hours at room temperature. The solids were filtered and washed with methylene chloride. The combined organic layer was evaporated under reduced pressure. The resulting residue was purified with CHROMATOREX Q-PACK S130 SIZE 20 (hexane: ethyl acetate = 50%:50% to 0%:100%) to obtain the aforementioned compound (934 mg, yield: 76%).
74% With potassium carbonate at 20℃; for 11h;
74% With potassium carbonate at 20℃; for 24.75h;
62% Stage #1: benzyl bromide; 1-amino-2-propene at 0 - 20℃; for 18h; Stage #2: With Sodium hydrogenocarbonate In lithium hydroxide monohydrate 1.3 A mixture of prop-2-en-l -amine (263mL) and l-(bromomethyl)benzene (100 g, 588.24mmol) was stirred at RT for 18 h (addition done at 00C). The reaction mixture was then quenched by the adding 500 mL of NaHCO3. The resulting aqueous solution was extracted with ether (3x500 mL) and the organics were combined, and dried over Na2SO4. The residue was purified by column chromatography on silica gel (eluting with a 1 : 100 EtOAc/PE solvent system). This resulted in 60 g (62%) of N-benzylprop- 2-en-l -amine as yellow oil.
54% With potassium carbonate In acetonitrile at 0℃; for 21h;
38% at 0 - 20℃; Inert atmosphere; Neat (no solvent);
at 0 - 20℃;
With potassium carbonate at 20℃; Inert atmosphere;
1.2 g With potassium carbonate at 20℃; for 16.75h; Description 32: N-benzylprop-2-en-l-amine (D32) Benzyl bromide (1 mL, 8.42 mmol) was added drop wise over 45 min to a mixture of K2CO3 (1.4 g, 10.10 mmol) and allylammine (5 mL, 66.8 mmol). The mixture was stirred at RT for 16 hrs then solid was filtered and filtrate was concentrated under reduced pressure to afford D32 (1.2 g) as a pale yellow oil used without further purification. Method 1; Rt: 0.85 min. m/z: 148 (M+H)+.

Reference: [1]Mukherjee, Santanu; List, Benjamin [Journal of the American Chemical Society, 2007, vol. 129, # 37, p. 11336 - 11337]
[2]Harvey, Daniel F.; Sigano, Dina M. [Journal of Organic Chemistry, 1996, vol. 61, # 7, p. 2268 - 2272]
[3]Petersen, Mette T.; Nielsen, Thomas E. [Organic Letters, 2013, vol. 15, # 8, p. 1986 - 1989]
[4]Takeda, Youhei; Okumura, Sota; Tone, Saori; Sasaki, Itsuro; Minakata, Satoshi [Organic Letters, 2012, vol. 14, # 18, p. 4874 - 4877,4]
[5]Fang, Weizhen; Presset, Marc; Guérinot, Amandine; Bour, Christophe; Bezzenine-Lafollée, Sophie; Gandon, Vincent [Organic Syntheses, 2016, vol. 92, p. 117 - 130]
[6]Kaafarni, Mustapha; Crozet, Michel P.; Surzur, Jean-Marie [Bulletin de la Societe Chimique de France, 1981, vol. 2, # 11-12, p. 449 - 457]
[7]Stec, Jozef; Thomas, Emma; Dixon, Sally; Whitby, Richard J. [Chemistry - A European Journal, 2011, vol. 17, # 17, p. 4896 - 4904]
[8]Current Patent Assignee: OITA UNIV INSTITUTE OF ADVANCED MEDICINE; OITA UNIVERSITY INSTITUTE OF ADVANCED MEDICINE - EP3838901, 2021, A1 Location in patent: Paragraph 0299; 0306
[9]Current Patent Assignee: OITA UNIV INSTITUTE OF ADVANCED MEDICINE; OITA UNIV INST OF ADVANCED MEDICINE - EP3978076, 2022, A1 Location in patent: Paragraph 0520; 0524
[10]Aurrecoechea, Jose M.; Fernandez, Alvaro; Gorgojo, Jose M.; Suero, Ruben [Synthetic Communications, 2003, vol. 33, # 5, p. 693 - 702]
[11]Song, Hongjian; Liu, Yongxian; Wang, Qingmin [Organic Letters, 2013, vol. 15, # 13, p. 3274 - 3277]
[12]Current Patent Assignee: KALYPSYS, INC. - WO2008/103615, 2008, A1 Location in patent: Page/Page column 41
[13]Kerres, Sabine; Plut, Eva; Malcherek, Simon; Rehbein, Julia; Reiser, Oliver [Advanced Synthesis and Catalysis, 2019] Kerres, Sabine; Plut, Eva; Malcherek, Simon; Rehbein, Julia; Reiser, Oliver [Advanced Synthesis and Catalysis, 2019, vol. 361, # 6, p. 1400 - 1407]
[14]Nicolai, Stefano; Piemontesi, Cyril; Waser, Jerome [Angewandte Chemie - International Edition, 2011, vol. 50, # 20, p. 4680 - 4683]
[15]Shapiro et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 3725,3726]
[16]Barbazanges, Marion; Meyer, Christophe; Cossy, Janine; Turner, Peter [Chemistry - A European Journal, 2011, vol. 17, # 16, p. 4480 - 4495]
[17]Ascic, Erhad; Hansen, Casper L.; Le Quement, Sebastian T.; Nielsen, Thomas E. [Chemical Communications, 2012, vol. 48, # 27, p. 3345 - 3347]
[18]Current Patent Assignee: ANTIOS THERAPEUTICS - WO2020/30781, 2020, A1 Location in patent: Page/Page column 64
  • 2
  • [ 106-95-6 ]
  • [ 100-46-9 ]
  • [ 4383-22-6 ]
YieldReaction ConditionsOperation in experiment
75% With potassium iodide In dimethyl sulfoxide at 0 - 20℃; for 18h;
75% With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 8h; N Example N Synthesis of Intermediate N-Benzylprop-2-en-1-amine Benzylamine (1.07 g, 10.0 mmol), potassium carbonate (2.8 g, 20.00 mmol) and DMF (30 mL) were added to a 100 mL three-necked flask, followed by 3-bromoprop-1-ene (1.2 g, 10.0 mmol). Adding to the reaction system, reacting at room temperature 25 ° C for 8 hours;Quenched with water (30 mL),The mixture was extracted with EtOAc (EtOAc m.The filtrate was removed under reduced pressure using a rotary evaporator.Purified by column chromatography (EtOAc/PE (v/v) = 1/5).A colorless liquid of 1.10 g was obtained in a yield: 75%.
50% With sodium iodide In dimethyl sulfoxide at 20℃; for 18h;
48% With sodium iodide In dimethyl sulfoxide at 0 - 20℃; for 18h; Inert atmosphere;
45.61% With potassium iodide In ethanol at 80℃; for 1h; Procedure To a stirred solution allyl bromide (1.00 g, 8.33 mmol) in ethanol (8.0 mL) were added benzyl amine (1.78 g, 16.66 mmol) and KI (1.38 g, 8.33 mmol) at room temperature. The resulting reaction mixture was stirred at 80 °C for 1 hour. Four further batches were prepared using the method above and combined for work up and purification. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The obtained crude material was purified by manual column chromatography using 60-120 mesh silica gel and eluted with 1.5% MeOH in DCM. Appropriate fractions were concentrated to afford N-benzylprop-2-en-1-amine (2.2 g, Yield: 45.61 %,).1H NMR: (MeOD, 400 MHz) δ 7.46 - 7.40 (m, 5H), 6.00 - 5.94 (m, 1H), 5.48 - 5.40 (m, 2H), 4.06 (s, 2H), 3.57 (d, J = 0.8Hz, 2H)
43% In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;
43% In dichloromethane at 0 - 25℃; for 24h;
With sodium hydroxide
In diethyl ether
With sodium hydride In N,N-dimethyl-formamide at 25℃; for 24h;
With N-ethyl-N,N-diisopropylamine In acetonitrile
75 %Chromat. With tetrabutylammonium bromide; sodium hydroxide In lithium hydroxide monohydrate at 15℃; for 4h; General Procedure for the General Procedure for the Selective N-Benzylation, Allylation, and Alkylation or N,N-Dibenzylation, Allylation, and Alkylation of Primary and Secondary Amines General procedure: SiO2-CuI (0.1 g,5 mol% Cu) was added to a mixture of amine (0.5 mmol), benzyl chloride, allyl bromide, or n-butyl chloride (0.5 mmol for N-substitution and 1 mmol for N,N-disubstitution), NaOH (2 mmol), and TBAB (0.25 mmol) in a round-bottom flask(25 mL) in water (4mL). The reaction mixture was stirred at 15°C (in the case of N-benzylation, allylation, or alkylation of primary amines,Table 2) or 70-100°C (in the case of N,N-dibenzylation, allylation, or alkylation of primary amines, Table 3), and 100°C(N-benzylation, allylation, and alkylation of secondary amines, Table 4) for an appropriate time. After completion of the reaction (monitored by thin-layer chromatography, TLC), the reaction mixture was triturated with EtOAc (20 mL) and the SiO2-CuI was filtered off. The product was obtained after removal of the solvent under reduced pressure followed by column chromatography or crystallization from EtOAc-petroleum ether.
With sodium iodide In dimethyl sulfoxide at 20℃; for 18h;
In tetrahydrofuran
With potassium carbonate; potassium iodide In acetonitrile at 60℃; Inert atmosphere;
With potassium carbonate In acetonitrile at 0 - 20℃; for 24h; 4.1 1) Reaction of benzylamine and allyl bromide Add 3.21g of benzylamine and 30mL of acetonitrile to a 100mL single-necked round bottom flask, then add 12.42g of potassium carbonate, use an ice-water bath, wait for the temperature to drop to 0, add 3.0g of allyl bromide dropwise. During the dripping process, keep the temperature no more than 10°C. After the allyl bromide dripping is finished, let the system react at room temperature for 24h. After the reaction is completed, the filtrate is vacuum filtered, and the filtrate is spin-dried under reduced pressure, and is separated by column chromatography with ethyl acetate: petroleum ether in a volume ratio of 1:10 to obtain a colorless oily product.
In neat (no solvent) at 20℃;

Reference: [1]Wang, Mei-Yan; Cao, Yu; Liu, Xi; Wang, Ning; He, Liang-Nian; Li, Si-Han [Green Chemistry, 2017, vol. 19, # 5, p. 1240 - 1244]
[2]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD; GUANGDONG HEC TECHNOLOGY HOLDING CO., LTD. - CN108689951, 2018, A Location in patent: Paragraph 0426; 0427; 0428
[3]Makino, Tatsuya; Itoh, Kenji [Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 395 - 405]
[4]Wang, Xiaoxia; Li, Jianyong; Yuan, Ting; You, Bingxin; Xie, Guanqun; Lv, Xin [Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 8984 - 8994]
[5]Current Patent Assignee: STORM THERAPEUTICS - WO2022/74391, 2022, A1 Location in patent: Paragraph 00320
[6]Huang, Shujian; Shao, Yinlin; Zhang, Lixin; Zhou, Xigeng [Angewandte Chemie - International Edition, 2015, vol. 54, # 48, p. 14452 - 14456][Angew. Chem., 2015, vol. 127, # 48, p. 14660 - 14664,5]
[7]Hou, Jinsong; Yang, Gaosheng; Chai, Zhuo [Journal of Organic Chemistry, 2022, vol. 87, # 1, p. 453 - 463]
[8]Babayan,A.T. et al. [Journal of general chemistry of the USSR, 1960, vol. 30, p. 2245 - 2249][Zhurnal Obshchei Khimii, 1960, vol. 30, p. 2263 - 2267]
[9]Jones,J.B.; Hysert,D.W. [Canadian Journal of Chemistry, 1971, vol. 49, p. 325 - 332] Mitsch,R.A.; Cromwell,N.H. [Journal of Organic Chemistry, 1960, vol. 25, p. 1719 - 1722]
[10]Yang, Yongzheng; Babiak, Peter; Reymond, Jean-Louis [Organic and Biomolecular Chemistry, 2006, vol. 4, # 9, p. 1746 - 1754]
[11]Location in patent: scheme or table Choi, Eunhyun; Lee, Chulho; Park, Jung Eun; Seo, Jeong Jea; Cho, Misun; Kang, Jong Soon; Kim, Hwan Mook; Park, Song-Kyu; Lee, Kiho; Han, Gyoonhee [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1218 - 1221]
[12]Shamim, Tahira; Kumar, Vineet; Paul, Satya [Synthetic Communications, 2014, vol. 44, # 5, p. 620 - 632]
[13]Hazarika, Debojit; Borah, Arun Jyoti; Phukan, Prodeep [Chemical Communications, 2019, vol. 55, # 10, p. 1418 - 1421]
[14]Choi, Goyeong; Jo, Seoyoung; Mun, Juyeon; Jeong, Yonguk; Kim, Seok-Ho; Jung, Jong-Wha [Molecules, 2019, vol. 24, # 24]
[15]Li, Jun; Yang, Yi; Liu, Yunxia; Liu, Qing; Zhang, Lizhi; Li, Xinjin; Dong, Yunhui; Liu, Hui [Organic Letters, 2021, vol. 23, # 8, p. 2988 - 2993]
[16]Current Patent Assignee: CHAOHU UNIVERSITY - CN109438327, 2021, B Location in patent: Paragraph 0093; 0097-0098
[17]Diaba, Faïza; Trenchs, Gisela [Organic and Biomolecular Chemistry, 2022, vol. 20, # 15, p. 3118 - 3123]
  • 4
  • [ 4383-22-6 ]
  • [ 38002-45-8 ]
  • [ 109828-51-5 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate In acetonitrile at 20℃; for 20h;
78% With sodium carbonate In ethanol for 6h; Ambient temperature;
  • 5
  • [ 4383-22-6 ]
  • [ 201230-82-2 ]
  • [ 5291-77-0 ]
  • 6
  • benzylidene allylamine [ No CAS ]
  • [ 4383-22-6 ]
YieldReaction ConditionsOperation in experiment
90% With trichlorosilane In N,N-dimethyl-formamide; toluene at 15 - 20℃; for 16h; Inert atmosphere;
85% With sodium tetrahydroborate In methanol at 0℃; for 0.333333h; Inert atmosphere;
83% With Benzeneselenol In chloroform for 0.166667h; Ambient temperature;
81% Stage #1: benzylidene allylamine With C21H39NPPd(1-)*C2F3O2(1-); phenylsilane In chloroform-d1 at 40℃; for 4h; Glovebox; Sealed tube; Stage #2: With water In chloroform-d1 Sealed tube; Glovebox; regioselective reaction;
With sodium tetrahydroborate In methanol for 24h; Ambient temperature;
With sodium tetrahydroborate In methanol for 0.5h; Ambient temperature; Yield given;
With sodium tetrahydroborate In methanol
With indium; ammonium chloride In ethanol for 11h; Heating;
With sodium tetrahydroborate
Multi-step reaction with 3 steps 1: Br2 / CH2Cl2 2: NaBH4 / methanol / Heating 3: 40 percent / lithium diallycuprate / diethyl ether / 6 h / -78 - 20 °C
Multi-step reaction with 3 steps 1.1: Br2 / CH2Cl2 2.1: NaBH4 / methanol / Heating 3.1: CuI / diethyl ether / cooling 3.2: 10 percent / diethyl ether / 19 h / -78 - 20 °C
With sodium tetrahydroborate In methanol at 0℃; for 1h;
With methanol; sodium tetrahydroborate at 20℃; for 3h; Cooling with ice; Inert atmosphere;
90 %Spectr. With [Tp(Me2)Rh(S2C6H4)(MeCN)]; hydrogen In tetrahydrofuran at 20℃; for 1h; chemoselective reaction;
956 mg With sodium cyanoborohydride In methanol at 0 - 20℃;
With sodium tetrahydroborate In methanol at 0 - 20℃; for 2h; Inert atmosphere; Preparation of N-allylbenzylamine: The N-allylbenzylamine was synthesized using a reported procedure. In a round bottom flask was placed at 0°C, 4.0 equiv. of MgSO4 in dry DCM (C = 0.2 mol/L) under argon, then 1.0 equiv. of benzaldehyde was added, followed by 1.1 equiv. of allylamine. The suspension was stirred at room temperature for 24 h, then the reaction mixture was filtrated and the solvent was removed under vaccum. The crude imine was used directly without purification in the next step. The oily residue was dissolved in MeOH (C = 1 mol/L) and 2.0 equiv. of sodium borohydride were added by small portions at 0 °C. The solution was stirred at room temperature for 2 h, then the solvent was evaporated and the reaction was quenched carefully with a saturated aqueous solution of ammonium chloride. The aqueous phase was extracted with DCM (3 times) and the combined organic phases were then dried with MgSO4, filtrated and the solvent was removed under vacuum. The resulting N-allylbenzylamine showed clean NMR spectra and was used without further purification.
Multi-step reaction with 2 steps 1.1: eosin Y / acetonitrile / 20 °C / Irradiation 2.1: dichloromethane / 2 h / 20 °C / Schlenk technique 2.2: 5 h / Cooling with ice; Schlenk technique
Multi-step reaction with 3 steps 1.1: eosin Y / acetonitrile / 20 °C / Irradiation 2.1: eosin Y / acetonitrile / 20 °C / Irradiation 3.1: dichloromethane / 2 h / 20 °C / Schlenk technique 3.2: 5 h / Cooling with ice; Schlenk technique
With sodium tetrahydroborate In methanol at 0℃; Inert atmosphere;
Multi-step reaction with 2 steps 1: [(2-diphenylphosphinocyclopentene-1-(2,6-dimethylphenyl)imine)Ni(allyl)]OTf / chloroform-d1 / 20 °C / Glovebox; Inert atmosphere 2: methanol; silica gel / Inert atmosphere

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[2]Kakaei, Saeed; Xu, Jiaxi [Organic and Biomolecular Chemistry, 2013, vol. 11, # 33, p. 5481 - 5490]
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[8]Banik; Hackfeld; Becker [Synthetic Communications, 2001, vol. 31, # 10, p. 1581 - 1586]
[9]Molander, Gary A.; Romero, Jan Antoinette C. [Tetrahedron, 2005, vol. 61, # 10, p. 2631 - 2643]
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[12]Location in patent: experimental part Zhou, Lijun; Yang, Qingang; Wang, Yong; Hu, Youhong; Luo, Xiaomin; Bai, Donglu; Li, Shukun [Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 8, p. 1147 - 1152]
[13]Sylvester, Kevin T.; Chirik, Paul J. [Journal of the American Chemical Society, 2009, vol. 131, # 25, p. 8772 - 8774]
[14]Misumi, Yoshiyuki; Seino, Hidetake; Mizobe, Yasushi [Journal of the American Chemical Society, 2009, vol. 131, # 41, p. 14636 - 14637]
[15]Benedetti, Erica; Lomazzi, Michela; Tibiletti, Francesco; Palmisano, Giovanni; Penoni, Andrea; Goddard, Jean-Philippe; Fensterbank, Louis; Malacria, Max [Synthesis, 2012, vol. 44, # 22, p. 3523 - 3533,11]
[16]Manick, Anne-Doriane; Berhal, Farouk; Prestat, Guillaume [Synthesis, 2016, vol. 48, # 21, p. 3719 - 3729]
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[18]Hall, Andrew M. R.; Broomfield-Tagg, Rachael; Camilleri, Matthew; Carbery, David R.; Codina, Anna; Whittaker, David T. E.; Coombes, Steven; Lowe, John P.; Hintermair, Ulrich [Chemical Communications, 2017, vol. 54, # 1, p. 30 - 33]
[19]Peilleron, Laure; Retailleau, Pascal; Cariou, Kevin [Advanced Synthesis and Catalysis, 2019, vol. 361, # 22, p. 5160 - 5169]
[20]Hossain, Istiak; Schmidt, Joseph A. R. [European Journal of Inorganic Chemistry, 2020, vol. 2020, # 19, p. 1877 - 1884]
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