[ CAS No. 332-48-9 ] {[proInfo.proName]}

Name: 332-48-9|1-(2-Bromoethoxy)-4-fluorobenzene|98%
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Quality Control of [ 332-48-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 332-48-9 ]

Product Details of [ 332-48-9 ]

CAS No. :	332-48-9	MDL No. :	MFCD00044739
Formula :	C₈H₈BrFO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JXSPKRUNMHMICQ-UHFFFAOYSA-N
M.W :	219.05	Pubchem ID :	2064171
Synonyms :

Calculated chemistry of [ 332-48-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.57
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.46
Log Po/w (XLOGP3) :	2.91
Log Po/w (WLOGP) :	3.02
Log Po/w (MLOGP) :	3.03
Log Po/w (SILICOS-IT) :	3.11
Consensus Log Po/w :	2.91

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.24
Solubility :	0.127 mg/ml ; 0.000579 mol/l
Class :	Soluble
Log S (Ali) :	-2.76
Solubility :	0.377 mg/ml ; 0.00172 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.09
Solubility :	0.018 mg/ml ; 0.000082 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 332-48-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P273	UN#:	N/A
Hazard Statements:	H302-H412	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 332-48-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 332-48-9 ]
Downstream synthetic route of [ 332-48-9 ]

[ 332-48-9 ] Synthesis Path-Upstream 1~1

1
[ 371-41-5 ]
[ 106-93-4 ]
[ 332-48-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide In water for 10 h; Reflux	Step 2: A 22.5percent aqueous sodium hydroxide solution (55 mL) was added to a mixture of 1,2-dibromoethane (112 g (0.60 mol)) and 4-fluorophenol (16.8 g (0.15 mol)), and the mixture was stirred 5 hours under heating at reflux. Sodium hydroxide (3.0 g (75 mmol)) was further added thereto and the mixture was stirred for 5 hours under heating at reflux. After completion of the reaction, the temperature was returned to room temperature, and the reaction solution was extracted three times with dichloromethane (100 mL). The whole organic layer was dried over Na₂SO₄ and the solvent was distilled away under reduced pressure. The residue was purified by a silica gel chromatography (petroleum ether: ethyl acetate = 10: 1) to obtain 1-(2-bromoethoxy)-4-fluorobenzene (compound-03) (29.7 g, 0.136 mol, yield 90percent).

Reference： [1] Patent: EP2357165, 2011, A1, . Location in patent: Page/Page column 18
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 495 - 500
[3] Russian Journal of Organic Chemistry, 2000, vol. 36, # 2, p. 254 - 257
[4] Archiv der Pharmazie, 2013, vol. 346, # 3, p. 180 - 188
[5] European Journal of Medicinal Chemistry, 1992, vol. 27, # 5, p. 545 - 549
[6] Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya, 1958, vol. 1, # 2, p. 82[7] Chem.Abstr., 1959, p. 1243
[8] Bulletin de la Societe Chimique de France, 1956, p. 185,186
[9] Journal of medicinal chemistry, 1966, vol. 9, # 2, p. 197 - 203
[10] Journal of Medicinal Chemistry, 1982, vol. 25, # 1, p. 57 - 63
[11] Central European Journal of Chemistry, 2013, vol. 11, # 11, p. 1757 - 1767
[12] European Journal of Medicinal Chemistry, 2014, vol. 81, p. 89 - 94

[ 332-48-9 ] Synthesis Path-Downstream 1~88

1
[ 332-48-9 ]
[ 865-47-4 ]
[ 351-93-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1956,p. 185,186

2
[ 6096-81-7 ]
[ 332-48-9 ]
[ 6096-72-6 ]

Reference： [1]Journal of medicinal chemistry,1966,vol. 9,p. 197 - 203

3
[ 554-84-7 ]
[ 332-48-9 ]
[ 79808-04-1 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 57 - 63

4
[ 19791-95-8 ]
[ 332-48-9 ]
[ 103197-02-0 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

5
[ 63327-49-1 ]
[ 332-48-9 ]
[ 103197-05-3 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

6
[ 332-48-9 ]
[ 145276-53-5 ]
[ 145276-55-7 ]

Reference： [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 545 - 549

7
[ 332-48-9 ]
[ 114997-84-1 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1719 - 1728

8
[ 100-97-0 ]
[ 332-48-9 ]
1-[2-(4-fluoro-phenoxy)-ethyl]-3,5,7-triaza-1-azonia-tricyclo[3.3.1.1^3,7]decane; bromide [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4591 - 4595

9
[ 332-48-9 ]
N,N-bis[2-(4'-fluorophenoxy)ethyl]amine [ No CAS ]
2-(4-fluorophenoxy)ethan-1-amine hydrochloride [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4591 - 4595

10
[ 764722-60-3 ]
[ 332-48-9 ]
4'-Trifluoromethyl-biphenyl-4-carboxylic acid ((S)-1-{(R)-3-[2-(4-fluoro-phenoxy)-ethylamino]-pyrrolidine-1-carbonyl}-pyrrolidin-3-yl)-methyl-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4450 - 4457

11
[ 104-58-5 ]
[ 332-48-9 ]
[ 144-62-7 ]
1-{3-[2-(4-fluorophenoxy)ethoxy]propyl}piperidine hydrogen oxalate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3522 - 3529

12
[ 332-48-9 ]
[ 57260-71-6 ]
[ 947695-05-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 24h;	To a solution of piperazine-1-carboxylic acid /er/-butyl ester (1.86 g, 10 mmol) and l-(2- bromoethoxy)-4-fluorobenzene (2.19 g, 10 mmol) in DMF (5 ml) was added CS2CO3 (7.5 g,20 mmol). The mixture was stirred at room temperature for a day, then quenched with water, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulphate, and concentrated to yield the title compound quantitatively as an oil (3.25 g) which was used without further purification.1H-NMR (400MHz, DMSO-d6): delta 1.39 (s, 9H), 2.42 (t, 4H), 2.69 (t, 2H), 3.31 (t, 4H), 4.04(t, 2H), 6.95 (m, 2H), 7.10 (t, 2H).

Reference： [1]Patent: WO2007/97871,2007,A2 .Location in patent: Page/Page column 13

13
[ 897391-14-9 ]
[ 332-48-9 ]
[ 1000922-57-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	b) 2-({4-Bromo-1-[2-(4-fluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2- methyl-propionic acid methyl esterTo 90 mg cesium carbonate and 92 mg 2-[(4-bromo-1-hydroxy-naphthalene-2- carbonyl)-amino]-2-methyl-propionic acid methyl ester in 1 ml abs. DMF 60 mg 4- fluorophenoxyethylbromide was added. After 16 h at room temperature the reaction was poured unto ice-water and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated in vacuo. After purification by RP-HPLC 61 mg of 2-({4-Bromo-1-[2-(4- fluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid methyl ester were obtained. _ _ _ . . _ - - c24H23BrFNO5 (504.36), LCMS (ESI): 504.05, 506.05 (MH+, bromo-pattern).

Reference： [1]Patent: WO2008/409,2008,A1 .Location in patent: Page/Page column 103

14
[ 934-32-7 ]
[ 332-48-9 ]
[ 364339-37-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 50℃;	Procedure B; 2-Aminobenzimidazole and K2CO3 (2 eq) dissolved in dry acetonitrile was (under N2) added the required aryl alkyl halide (1 eq) and stirred at 500C overnight. After cooling to rt, water was added and the mixture extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give the crude N-alkylated 2-aminobenzimidazole which was purified by preparative LC-MS or, alternatively, by column chromatography.This intermediate was subsequently, in acetonitrile or DMF and under a nitrogen atmosphere, cooled on ice, added NaH (1.2 eq) and allowed to heat to rt. To the reaction mixture was added the required substituted aryl alkyl halide and stirring was continued at room temperature over night. Water was added and the mixture extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give the crude dialkylated 2-aminobenzimidazole which was purified by preparative LC-MS or, alternatively, by column chromatography.An example of Procedure B, the preparation of [2-(4-fluorophenoxy)ethyl]- {1-[2-(4-fluorophenoxy)ethyl]-1 H-benzoimidazol-2-yl}amine, is shown in Scheme 2.; Example 1; [2-(4-Fluorophenoxy)ethyl]-{1-[2-(4-fluorophenoxy)ethyl]-1 W-benzoimidazol-2- yl}amine; The title compound was prepared in two steps from 2-aminobenzimidazole and 1-(2-bromoethoxy)-4-fluorobenzene as described in Procedure B. The crude product was purified by preparative LC-MS to give the title compound as the free base(yellowish solid). MS(ES+) m/z 410 ([M+1]+, 100); HR-MS: 410.169900 ([M+1]+,C23H22F2N3O2; calc. 410.168008).

Reference： [1]Patent: WO2008/3752,2008,A1 .Location in patent: Page/Page column 20-21

15
[ 332-48-9 ]
[2-(4-fluorophenoxy)ethyl]-{1-[2-(4-fluorophenoxy)ethyl]-1H-benzoimidazol-2-yl}amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Procedure B; 2-Aminobenzimidazole and K2CO3 (2 eq) dissolved in dry acetonitrile was (under N2) added the required aryl alkyl halide (1 eq) and stirred at 500C overnight. After cooling to rt, water was added and the mixture extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give the crude N-alkylated 2-aminobenzimidazole which was purified by preparative LC-MS or, alternatively, by column chromatography.This intermediate was subsequently, in acetonitrile or DMF and under a nitrogen atmosphere, cooled on ice, added NaH (1.2 eq) and allowed to heat to rt. To the reaction mixture was added the required substituted aryl alkyl halide and stirring was continued at room temperature over night. Water was added and the mixture extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give the crude dialkylated 2-aminobenzimidazole which was purified by preparative LC-MS or, alternatively, by column chromatography.An example of Procedure B, the preparation of [2-(4-fluorophenoxy)ethyl]- {1-[2-(4-fluorophenoxy)ethyl]-1 H-benzoimidazol-2-yl}amine, is shown in Scheme 2.; Example 1; [2-(4-Fluorophenoxy)ethyl]-{1-[2-(4-fluorophenoxy)ethyl]-1 W-benzoimidazol-2- yl}amine; The title compound was prepared in two steps from 2-aminobenzimidazole and 1-(2-bromoethoxy)-4-fluorobenzene as described in Procedure B. The crude product was purified by preparative LC-MS to give the title compound as the free base(yellowish solid). MS(ES+) m/z 410 ([M+1]+, 100); HR-MS: 410.169900 ([M+1]+,C23H22F2N3O2; calc. 410.168008).

Reference： [1]Patent: WO2008/3752,2008,A1 .Location in patent: Page/Page column 20-21

16
[ 934-32-7 ]
[ 332-48-9 ]
1,3-bis-[2-(4-fluorophenoxy)ethyl]-1,3-dihydrobenzoimidazol-2-ylideneamine hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 50℃;	Procedure A; 2-Aminobenzimidazole and K2CO3 (4 eq) dissolved in dry acetonitrile was(under N2) added the required aryl alkyl halide (2 eq) and stirred at 500C overnight. After cooling to rt, water was added and the mixture extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give the crude product which was purified by preparative LC-MS or, alternatively, by column chromatography and/or recrystallization.An example of Procedure A, the preparation of 1 ,3-bis-(4-chlorophenoxy- methyl)-1 ,3-dihydrobenzoimidazol-2-ylideneamine, is shown in Scheme 1.; Example 2; 1 ,3-Bis-[2-(4-fluorophenoxy)ethyl]-1 ,3-dihydrobenzoimidazol-2-ylideneamine; The title compound was prepared from 2-aminobenzimidazole and 1-(2- bromoethoxy)-4-fluorobenzene by Procedure A. The crude product was purified by preparative LC-MS to give the title compound as a hydrobromide salt (white solid). MS(ES+) m/z 410 ([M+1]+, 100); HR-MS: 410.170000 ([M+1]+, C23H22F2N3O2; calc.410.168008).

Reference： [1]Patent: WO2008/3752,2008,A1 .Location in patent: Page/Page column 19; 21

17
[ 332-48-9 ]
[ 1074-82-4 ]
[ 725703-13-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	In N,N-dimethyl-formamide; at 100℃; for 1h;	A mixture of 5 g (22.8 mmol) of 1-(2-bromoethoxy)-4-fluorobenzene (6A) and4.23 g of potassium phthalimide (22.8 mmol) in 21 ml of DMF is heated for 1 hour (Oil bath temperature = 1000C).When the medium has cooled to room temperature, a solution of saturated sodium chloride (NaCI) (about 150 ml) and of ethyl acetate (about 100 ml) is added. After separation of the phases by settling, the aqueous phase is extracted with3 x 80 ml of ethyl acetate and the combined organic phases are washed with 2 * 80 ml of NaCI and 2 x 80 ml of water.The organic phase is dried over magnesium sulfate (MgSO4) and concentrated. 6.20 g of a white solid are obtained. YId: 95% m.p. = 1200C1H NMR (DMSO delta in ppm): 4.12 (t, 2H); 4.36 (t, 2H); 7.08 (d, 2H); 7.25 (t, 2H); 8.03 (s, 4H).Purity = 98% MS (APCI) m/z: 286 [M+H]+

Reference： [1]Patent: WO2008/6432,2008,A1 .Location in patent: Page/Page column 33
[2]Central European Journal of Chemistry,2013,vol. 11,p. 1757 - 1767
[3]Archiv der Pharmazie,2019,vol. 352

18
[ 1009378-48-6 ]
[ 332-48-9 ]
2-{1-[2-(4-fluoro-phenoxy)-ethyl]-1H-pyrazol-3-yl}-4-methyl-thiazole-5-carboxylic acid benzylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With potassium carbonate; In dimethyl sulfoxide; at 90℃; for 16h;	A solution of 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid benzylamide (0.2 g, 0.67 mmol) in dimethyl sulfoxide (5 mL) was treated with 4-fluorophenoxyethyl bromide (0.14 g, 0.67 mmol) and potassium carbonate (0.30 g, 2.0 mmol), and the reaction mixture was heated to 90 0C for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), and washed with brine (2 x 50 mL). The organic phase was dried (Na2SC^) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel (methylene chloride:methanol, 95:5) to provide 2-{l-[2-(4-fluoro-phenoxy)-ethyl]-lH-pyrazol-3-yl}-4-methyl-thiazole- 5-carboxylic acid benzylamide (0.071 g, 51% yield) as a white solid.

Reference： [1]Patent: WO2008/24390,2008,A2 .Location in patent: Page/Page column 111

19
[ 332-48-9 ]
[2-(4-fluoro-phenoxy)-ethyl]-carbamic acid isobutyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4591 - 4595

20
[ 332-48-9 ]
CRA-9249 [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4591 - 4595
[2]Tetrahedron Letters,2006,vol. 47,p. 4591 - 4595

21
[ 332-48-9 ]
2-(difluoro-{6-[2-(4-fluoro-phenoxy)-ethylcarbamoyl]-1-methyl-1<i>H</i>-benzoimidazol-2-yl}-methyl)-4,6-difluoro-benzoimidazole-1-carboxylic acid isopropyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4591 - 4595

22
[ 332-48-9 ]
2-(difluoro-{6-[2-(4-fluoro-phenoxy)-ethylcarbamoyl]-1-methyl-1<i>H</i>-benzoimidazol-2-yl}-methyl)-4,6-difluoro-benzoimidazole-1-carboxylic acid isobutyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4591 - 4595

23
[ 332-48-9 ]
[ 6096-89-5 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4591 - 4595
[2]Central European Journal of Chemistry,2013,vol. 11,p. 1757 - 1767
[3]Archiv der Pharmazie,2019,vol. 352

24
[ 332-48-9 ]
[ 79808-17-6 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 57 - 63

25
[ 332-48-9 ]
7-[2-(4-Fluoro-phenoxy)-ethoxy]-4-hydroxy-quinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 57 - 63

26
[ 332-48-9 ]
7-[2-(4-Fluoro-phenoxy)-ethoxy]-4-hydroxy-quinoline-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 57 - 63

27
[ 332-48-9 ]
2-({3-[2-(4-Fluoro-phenoxy)-ethoxy]-phenylamino}-methylene)-malonic acid diethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 57 - 63

28
[ 332-48-9 ]
[ 114997-34-1 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1719 - 1728

29
[ 332-48-9 ]
[ 67146-05-8 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

30
[ 332-48-9 ]
[ 103196-96-9 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

31
[ 332-48-9 ]
[ 103197-08-6 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

32
[ 332-48-9 ]
[ 90477-47-7 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

33
[ 332-48-9 ]
[ 103196-95-8 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

34
[ 332-48-9 ]
[ 103197-07-5 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

35
[ 332-48-9 ]
[ 103197-09-7 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

36
[ 332-48-9 ]
[ 103197-13-3 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

37
[ 332-48-9 ]
[ 103197-16-6 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3587 - 3591

38
[ 332-48-9 ]
[ 121773-17-9 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 5493 - 5496

39
[ 332-48-9 ]
[ 121773-22-6 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 5493 - 5496

40
[ 332-48-9 ]
[ 121843-14-9 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 5493 - 5496

41
[ 332-48-9 ]
2-Amino-4-(4-fluoro-phenoxy)-butyric acid methyl ester; hydrochloride [ No CAS ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 5493 - 5496

42
[ 332-48-9 ]
[ 111949-95-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 547 - 552

43
[ 332-48-9 ]
[ 1644-58-2 ]

Reference： [1]Journal of medicinal chemistry,1966,vol. 9,p. 197 - 203

44
[ 302523-50-8 ]
[ 332-48-9 ]
1-[2-(4-fluorophenoxy)ethyl]-4-[2-[N-methyl-N-(4-isopropoxyphenyl)amino]ethyl]piperidin-4-ol [ No CAS ]

Reference： [1]Patent: EP1182192,2002,A1 .Location in patent: Example 116

45
3-benzyl-6-mercapto-5-methyl-1H-pyrimidine-2,4-dione [ No CAS ]
[ 332-48-9 ]
3-benzyl-6-[3-(4-fluoro-phenyl)-3-oxo-propylsulfanyl]-5-methyl-1H-pyrimidine-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In DMF (N,N-dimethyl-formamide); at 60℃; for 24h;	In an 8 mL screw cap vial was added a solution of [3-BENZYL-6-MERCAPTO-5-] methyl-lH-pyrimidine-2, 4-dione, (0.025 g, 0.1 mmol) in dimethylformamide, [DMF] [(1] mL) and a solution of an alkyl bromide (0.15 mmol) in [DMF] (300 [GEL).] The vial was capped and the reaction mixture was shaken for 24 hours at [60C.] The solvent was removed under vacuum. Purification was carried out via reverse- phase [HPLC] (3% n-propanol in acetonitrile and [3%] n-propanol in water as the eluent; C-18 column).

Reference： [1]Patent: WO2004/14868,2004,A2 .Location in patent: Page 92-93, 95

46
[ 332-48-9 ]
[ 30033-24-0 ]
2-(4-fluorophenoxy)-ethyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydrogencarbonate; In N,N-dimethyl acetamide; at 65℃;	A suspension of N-Boc- (L)-dopa 67.27 mmol), 2-(4- fluorophenoxy) ethyl bromide (0.95 eq) and potasium bicarbonate (1.1 eq) in DMA (100 mL) was stirred at 65 C overnight. The reacted mixture was diluted with EtOAc (750 mL), washed with water (2x200 mL) and saturated NaHC03 (2x200 mL), brined, dried over Na2S04, concentrated under reduced pressure, and purified by column chromatography on silica gel (60 A, 200-400 Mesh) eluting with 3:7 EtOAc/Hexane to give a clear oil. [00176] The oil was dissolved in a solution of HCl/1,4-dioxane (4.OM, 100 mL), and the mixture was stirred at room temperature for 1 hour before concentrating under reduced pressure to a solid. After dissolving the solid in a minimal amount of acetonitrile (100 mL), the solution was chilled to 4 C, and the resulting white precipitate was collected on a Buchner funnel, washed with diethyl ether (3x50 mL) and dried under high vacuum to afford the title compound as a solid: ¹H NMR (d6-DMSO) : No. 2.92 (m, 2H), 4.14 (m, 2H), 4.21 (t, J = 6.4 Hz, 1H), 4.42 (t, J = 4.4 Hz, 2H), 6.43 (d, J = 7.6 Hz, 1H), 6.59 (s, 1H), 6.60 (d, J = 8.0 Hz, 1H), 6.94 (m, 2H), 7.12 (3, 2H), 8.40 (s, 3H), 8.90 (m, 2H). MS (ESI) m/z 336 (M+H) (at) and 334 (M-H)-.

Reference： [1]Patent: WO2005/121070,2005,A1 .Location in patent: Page/Page column 39

47
[ 2295-31-0 ]
[ 332-48-9 ]
5-[2-(4-fluorophenoxy)ethyl]-2,4-thiazolidinedione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; n-butyllithium; In tetrahydrofuran; water; ethyl acetate;	EXAMPLE III 5-[2-(4-fluorophenoxy)ethyl]-2,4-thiazolidinedione (I) (according to route C) 33.4 g of 2,4-thiazolidinedione are dissolved in 1700 ml of tetrahydrofuran, under an inert atmosphere, and while the temperature of the reaction medium is maintained at -78 C, 228 ml of butyllithium (2.5 M hexane) are added dropwise. The temperature is allowed to rise to 20 C. and the mixture is stirred for 2 h at this temperature. It is cooled to -78 C. and 31.2 g of 1-(2-bromoethoxy)-4-fluorobenzene in solution in 600 ml of tetrahydrofuran are added dropwise. The temperature is then allowed to rise to room temperature and the mixture is stirred for 20 h at this temperature. The reaction medium is poured over 2300 ml of 2 N hydrochloric acid. The organic phase is decanted and concentrated. The residue is taken up in 800 ml of ethyl acetate and 1000 ml of water. The organic phase is decanted, washed 4 times with water, dried over sodium sulfate and evaporated to give an oil which is purifed on silica, eluding with a dichloromethane/acetone (97/3 by volume) mixture. The product obtained is recrystallized from diisopropyl ether. 8.5 g of 5-[2-(4-fluorophenoxy)ethyl]-2,4-thiazolidinedione are obtained in the form of a white solid whose melting point is 94-96 C.

Reference： [1]Patent: US2001/7875,2001,A1

48
tert-butyl 8,9-dichloro-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate [ No CAS ]
[ 332-48-9 ]
ammonium chloride [ No CAS ]
tert-butyl 8,9-dichloro-6-[2-(4-fluorophenoxy)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.43 g (78%)	In N,N-dimethyl-formamide; mineral oil;	Preparation 85 Preparation of tert-Butyl 8,9-dichloro-6-[2-(4-fluorophenoxy)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate To a solution of tert-butyl 8,9-dichloro-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.40 g, 1.1 mmol) in DMF (5 mL), sodium hydride (60% dispersion in mineral oil, 68 mg, 1.7 mmol) was added. After 25 min, 4-fluorophenoxy ethyl bromide (0.34 mL, 2.3 mmol) was added. The reaction was quenched with saturated aqueous NH4Cl after 2 h and extracted with EtOAc (3*15 mL). The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M) with heptane/EtOAc (gradient, 9:1 to 17:3) to give 0.43 g (78%) of a white foam: 1H NMR (300 MHz, CDCl3) delta 7.51 (d, J=3.8 Hz, 1H), 7.40 (d, J=6.0 Hz, 1H), 6.92 (t, J=8.7 Hz, 2H), 6.70 (m, 2H), 4.40 (t, J=5.3 Hz, 2H), 4.13 (t, J=5.3 Hz, 4H), 3.69 (m, 4H), 3.08 (m, 2H), 2.90 (m, 2H), 1.48 (s, 9H); IR (diffuse reflectance) 1687, 1505, 1468, 1414, 1366, 1296, 1268, 1248, 1218, 1169, 1114, 1105, 865, 827, 746 cm-1; MS (ES+) m/z 493 (M+H+), 516, 515, 366, 364, 265, 253, 138, 94, 91, 85; Anal. Calcd for C25H27Cl2FN2O3: C, 60.86; H, 5.51; N, 5.68, found: C, 60.91; H, 5.61; N, 5.64.

Reference： [1]Patent: US2002/77318,2002,A1

49
tert-butyl 9,10-dichloro-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate [ No CAS ]
[ 332-48-9 ]
ammonium chloride [ No CAS ]
tert-butyl 9,10-dichloro-6-[2-(4-fluorophenoxy)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.46 g (82%)	In N,N-dimethyl-formamide; mineral oil;	Preparation 88 Preparation of tert-Butyl 9,10-dichloro-6-[2-(4-fluorophenoxy)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate Sodium hydride (60% dispersion in mineral oil, 68 mg, 1.7 mmol) was added to a solution of tert-butyl 9,10-dichloro-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.40 g, 1.1 mmol) in DMF (6 mL). After 25 min, 4-fluorophenoxy ethyl bromide (0.34 mL, 2.3 mmol) was added. The reaction was quenched with saturated aqueous NH4Cl after 22 h and extracted with EtOAc (3*15 mL). The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M) with heptane/EtOAc (17:3) to give 0.46 g (82%) of a white solid: mp 163.5-165.5 C.; 1H NMR (300 MHz, CDCl3) delta 7.16 (m, 2H), 6.92 (m, 2H), 6.70 (m, 2H), 4.44 (m, 2H), 4.12 (m, 2H), 3.73 (m, 4H), 3.51 (m, 2H), 3.12 (m, 2H), 1.48 (s, 9H); IR (diffuse reflectance) 1675, 1507, 1449, 1405, 1365, 1354, 1298, 1249, 1242, 1221, 1209, 1170, 1120, 835, 828 cm-1; MS (FAB) m/z 493 (M+H+), 494, 493, 492, 439, 438, 437, 436, 435, 57, 42; HRMS (EI) calcd for C25H27Cl2FN2O3 492.1383, found 492.1385; Anal. Calcd for C25H27Cl2FN2O3: C, 60.86; H, 5.51; N, 5.68, found: C, 60.93; H, 5.60 N, 5.69.

Reference： [1]Patent: US2002/77318,2002,A1

50
[ 498-00-0 ]
[ 332-48-9 ]
{4-[2-(4-fluoro-phenoxy)-ethoxy]-3-methoxy-phenyl}-acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; water;	Example B1.1 {4-[2-(4-Fluoro-phenoxy)-ethoxy]-3-methoxy-phenyl}-acetonitrile A mixture of 4-hydroxy-3-methoxy-benzyl alcohol (14.7 g) and sodium cyanide (5 g) in dimethylformamide (200 ml) is stirred under an atmosphere of nitrogen for 3 hours at +1 20 C. The mixture is then cooled to +100 C. and 1-(2-bromo-ethoxy)-4-fluoro-benzene (25 g) is added in one portion. The mixture is stirred at +100 C. for another 4 hours. Upon cooling water (800 ml) is added. The mixture is extracted with ethyl acetate (2500 ml). The organic phases are washed with brine (2500 ml), dried (MgSO4) and evaporated. The residue is recrystallized from ethyl acetate/hexane. {4-[2-(4-Fluoro-phenoxy)-ethoxy]-3-methoxy-phenyl}-acetonitrile is obtained, m.p. 126-128 C.

Reference： [1]Patent: US2002/82452,2002,A1

51
[ 31252-42-3 ]
[ 332-48-9 ]
[ 584-08-7 ]
4-Benzyl-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	EXAMPLE 103 4-Benzyl-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride STR139 From a mixture of 4-benzylpiperidine (500 mg, 2.85 mmol), 2-(4-fluorophenoxy)ethyl bromide (655 mg, 2.99 mmol) and K2 CO3 (413 mg, 2.99 mmol) in CH3 CN (20 mL) was obtained the title compound as a fluffy, colorless, crystalline solid (395 g, 79%): mp 165-167 C., 1 H NMR (CDCl3) 1.70-1.90 (m, 3H), 1.94-2.14 (m, 2H), 2.59 (d, J=7.2 Hz, 2H), 2.65-2.85 (m, 2H), 3.20-3.50 (m, 2H), 3.65 (d, J=12 Hz, 2H), 4.49 (t, J=4.5 Hz, 2H), 6.76-7.30 (m, 9H), 12.47 (bs, 1H); Anal. Calcd for C20 H25 ClFNO: C, 68.66; H, 7.20; N, 4.00. Found: C, 68.66; H, 7.11; N, 3.98.

Reference： [1]Patent: US6124323,2000,A

52
[ 332-48-9 ]
[ 584-08-7 ]
[ 92822-01-0 ]
1-(2-(4-Fluorophenoxy)ethyl)-4-(4-methylbenzyl)piperidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	EXAMPLE 116 1-(2-(4-Fluorophenoxy)ethyl)-4-(4-methylbenzyl)piperidine hydrochloride STR152 From a mixture of 4-(4-methylbenzyl)piperidine (500 mg, 2.21 mmol), 2-(4-fluorophenoxy)ethyl bromide (508 mg, 2.32 mmol) and K2 CO3 (626 mg, 4.53 mmol) in CH3 CN (20 mL) was obtained the title compound as colorless plates (293 mg, 63%), mp 189-191 C., 1 H NMR (CDCl3) 1.60-2.12 (m, 5H), 2.31 (s, 3H), 2.57 (d, J=7.2 Hz, 2H), 2.62-2.82 (m, 2H), 3.20-3.55 (m, 2H), 3.65 (d, J=12 Hz, 2H), 4.51 (t, J=4.5 Hz, 2H), 6.78-6.84 (m, 2H), 6.92-7.02 (m, 6H), 7.08 (d, J=8.1 Hz, 2H), 12.56 (bs, 1H); Anal. Calcd for C21 H27 ClFNO: C, 69.31; H, 7.48; N, 3.85. Found: C, 69.49; H, 7.39; N, 3.88.

Reference： [1]Patent: US6124323,2000,A

53
4-(4-chlorobenzyl)piperidine hydrochloride [ No CAS ]
[ 332-48-9 ]
[ 584-08-7 ]
4-(4-chlorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrogenchloride; In methanol; acetonitrile;	B) 4-(4-Chlorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrobromide. A mixture of 4-(4-chlorobenzyl)piperidine hydrochloride (1.00 g, 4.06 mmol), 2-(4-fluorophenoxy)ethyl bromide (933 mg, 4.26 mmol) and K2 CO3 (1.15 g, 8.32 mmol) in CH3 CN (30 mL) was stirred at reflux under N2 for 3 d. The reaction was allowed to cool to 25 C. The reaction was then added to 100% HCl (100 mL) and extracted with CHCl3 (350 mL). The extract was washed with 5% NH4 OH (250 mL), filtered through cotton and the solvent removed on a rotoevap to give a colorless oil. The product was purified chromatographically on silica gel (2.5*30 cm). Elution with CHCl3 removed the more mobile impurities. Elution with 2% EtOH/99% CHCl3 removed the product. The solvent was removed from the product fractions on a rotoevap to give a colorless solid. The solid was dissolved in warm MeOH (10 mL), filtered through Celite and the MeOH removed on a rotoevap to give an colorless solid. The solid was dried in vacuo (0.005 Torr, 25 C.) to give an colorless solid (1.23 g, 87%): mp 85-87.5 C.; 1 H NMR (CDCl3) delta 1.25-1.68 (m, 5 H), 2.04 (t, J=12 Hz, 2 H), 2.50 (d, J=6.9 Hz, 2 H), 2.76 (t, J=6.0 Hz, 2 H), 2.97 (d, J=11 Hz, 2 H), 4.05 (t, J=6.0 Hz, 2 H), 6.77-7.00 (m, 4 H), 7.06 (d, J=8.1 Hz, 2 H), 7.24 (d, J=8.1 Hz, 2 H).

Reference： [1]Patent: US6124323,2000,A

54
[ 332-48-9 ]
[ 584-08-7 ]
4-(3-fluorobenzyl)piperidine hydrochloride [ No CAS ]
4-(3-Fluorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	EXAMPLE 113 4-(3-Fluorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride STR149 From a mixture of 4-(3-fluorobenzyl)piperidine hydrochloride (500 mg, 2.18 mmol), 2-(4-fluorophenoxy)ethyl bromide (501 mg, 2.29 mmol) and K2 CO3 (615 mg, 4.45 mmol) in CH3 CN (20 mL) was obtained the title compound as a fluffy, colorless, crystalline solid (360 mg, 81%): mp 155-157 C., 1 H NMR (CDCl3) 1.65-1.90 (m, 3H), 1.98-2.16 (m, 2H), 2.62 (d, J=7.2 Hz, 2H), 2.65-2.85 (m, 2H), 3.20-3.53 (m, 2H), 3.67 (d, J=12 Hz, 2H), 4.51 (t, J=4.5 Hz, 2H), 6.78-7.10 (m, 7H), 7.19-2.28 (m, 1H), 12.64 (bs, 1H); Anal. Calcd for C20 H24 ClF2 NO: C, 65.30; H, 6.58; N, 3.81. Found: C, 65.35; H, 6.58; N, 3.77.

Reference： [1]Patent: US6124323,2000,A

55
[ 193355-32-7 ]
[ 332-48-9 ]
[ 584-08-7 ]
4-(2-fluorobenzyl)piperidine hydrochloride [ No CAS ]
4-(2-Fluorobenzyl)1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	D) 4-(2-Fluorobenzyl)l-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride. From A mixture of 4-(2-fluorobenzyl)piperidine hydrochloride (500 mg, 2.18 mmol), 2-(4-fluorophenoxy)ethyl bromide (502 mg, 2.29 mmol) and K2 CO3 (618 mg, 4.47 mmol) in CH3 CN (20 mL) was obtained the title compound as a colorless crystalline solid (470 mg, 64%), mp 159-160 C. 1 H NMR (CDCl3) 1.70-2.22 (m, 5H), 2.62-2.88 (m, 4H), 3.20-3.50 (m, 2H), 3.60-3.75 (m, 2H), 4.52 (t, J=4.5 Hz, 2H), 6.78-7.28 (m, 8H), 12.64 (bs, 1H); Anal. Calcd for C20 H24 ClF2 NO: C, 65.30; H, 6.58; N, 3.81. Found: C, 65.25; H, 6.46; N, 3.74.

Reference： [1]Patent: US6124323,2000,A

56
4-((5,6,7,8-tetrahydro-2-naphthyl)methyl)piperidine hydrochloride [ No CAS ]
[ 332-48-9 ]
[ 584-08-7 ]
1-(2-(4-Fluorophenoxy)ethyl)-4-((5,6,7,8-tetrahydro-2-naphthyl)methyl)piperidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 140 1-(2-(4-Fluorophenoxy)ethyl)-4-((5,6,7,8-tetrahydro-2-naphthyl)methyl)piperidine hydrochloride STR176 The title compound was prepared from 4-((5,6,7,8-tetrahydro-2-naphthyl)methyl)piperidine hydrochloride (250 mg, 940 mumol), 2-(4-fluorophenoxy)ethyl bromide (216 mg, 987 mumol) and K2 CO3 (266 mg, 1.93 mmol) as a colorless solid (220 mg): mp 181-183 C.; 1 H NMR (CDCl3) 1.60-2.12 (m, 9H), 2.54 (d, J=7.2 Hz, 2H), 2.65-2.81 (m, 6H), 3.20-3.55 (m, 2H), 3.59-3.71 (m, 2H), 4.52 (t, J=4.2 Hz, 2H), 6.77-7.01 (m, 7H), 12.55 (bs, 1H); Anal. Calcd for C24 H31 ClFNO: C, 71.36; H, 7.74; N, 3.47. Found: C, 71.30; H, 7.78; N, 3.39.

Reference： [1]Patent: US6124323,2000,A

57
[ 193357-83-4 ]
[ 332-48-9 ]
[ 584-08-7 ]
1-(2-(4-Fluorophenoxy)ethyl)-4-((2-naphthyl)methyl)piperidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 142 1-(2-(4-Fluorophenoxy)ethyl)-4-((2-naphthyl)methyl)piperidine hydrochloride STR178 The title compound was prepared from 4-((2-naphthyl)methyl)piperidine hydrochloride (150 mg, 573 mumol), 2-(4-fluorophenoxy)ethyl bromide (132 mg, 602 mumol) and K2 CO3 (162 mg, 1.17 mmol) as a colorless solid (126 mg): mp 170-172 C.; 1 H NMR (CDCl3) 1.60-1.92 (m, 3H), 2.02-2.41 (m, 2H), 2.65-2.90 (m, 4H), 3.45-3.55 (m, 2H), 3.60-3.71 (m, 2H), 4.51 (t, J=4.2 Hz, 2H), 6.77-7.01 (m, 4H), 7.25 (d, J=6.0 Hz, 1H), 7.40-7.51 (m, 2H), 7.57 (s, 1H), 7.72-7.84 (m, 3H) 12.64 (bs, 1H). Anal. Calcd for C24 H27 ClFNO: C, 72.08; H, 6.80; N, 3.50. Found: C, 71.73; H, 6.64; N, 3.34.

Reference： [1]Patent: US6124323,2000,A

58
[ 6936-90-9 ]
[ 332-48-9 ]
[ 584-08-7 ]
2-(4-Chlorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	B) 2-(4-Chlorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride. From a mixture of 2-(4-chlorobenzyl)piperidine hydrochloride (500 mg, 2.03 mmol), 2-(4-fluorophenoxy)ethyl bromide (467 mg, 2.13 mmol) and K2 CO3 (575 mg, 4.16 mmol) in CH3 CN (20 mL) the free base of the title compound was obtained as an amber oil (445 mg, 63%): 1 H NMR (CDCl3) 1.15-1.35 (m, 2H), 1.42-1.70 (m, 4H), 2.42-3.20 (m, 7H), 3.95-4.13 (m, 2H), 6.82-7.02 (m, 4H), 7.10 (d, J=8.4 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H). The hydrochloride was obtained as a colorless powder (395 mg, 80%), mp 163-165 C.; 1 H NMR (CDCl3) 1.30-2.35 (m, 6H), 2.62-3.80 (m, 7H), 4.30-4.70 (m, 2H), 6.82-7.32 (m, 8H), 12.67 and 12.83 (overlapping bs, 1H); Anal. Calcd for C20 H24 Cl2 FNO: C, 62.51; H, 6.29; N, 3.64. Found: C, 62.51; H, 6.42; N, 3.47.

Reference： [1]Patent: US6124317,2000,A

59
[ 37581-26-3 ]
[ 332-48-9 ]
1-(2-(4-Fluorophenoxy)ethyl)-4-(4-methoxybenzyl)piperidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		B) 1-(2-(4-Fluorophenoxy)ethyl)-4-(4-methoxybenzyl)piperidine hydrochloride. This compound was prepared in a manner similar to example 25. From 4-(4-methoxybenzyl)piperidine (500 mg, 2.44 mmol) and 2-(4-fluorophenoxy)ethyl bromide (561 mg, 2.56 mmol) there was obtained the hydrochloride salt as colorless plates: mp 171-172 C.; 1 H NMR (CDCl3) 1.55-2.18 (m, 5 H), 2.50-2.82 (m, 4 H), 3.25-3.70 (m, 4 H), 3.77 (s, 3 H), 4.50 (t, J=3.6 Hz, 2 H), 6.75-7.07 (m, 8 H), 12.56 (bs, 1 H). Anal. Calcd for C21 H27 ClFNO2: C, 66.39; H, 7.16; N, 3.69. Found: C, 66.52; H, 7.29; N, 3.68.

Reference： [1]Patent: US6124323,2000,A

60
[ 332-48-9 ]
[ 177-11-7 ]
[ 78-93-3 ]
[ 146993-08-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;	EXAMPLE 2 Compound No. 2 2-[1-[2-(4-Fluorophenoxy)ethyl]piperidin-4-ylamino]pyrimidine-4-carboxamide, hydrochloride. 2.1 8-[2-(4-Fluorophenoxy)ethyl]-1,4-dioxa-8-azaspiro-[4.5]decane. 21.91 g (0.1 mol) of 2-(4-fluorophenoxy)ethyl bromide, 14.32 g (0.1 mol) of 1,4-dioxa-8-azaspiro[4.5]decane and 20.73 g (0.15 mol) of potassium carbonate are introduced into 250 ml of 2-butanone and the mixture is heated at boiling for 7 hours. The mixture is cooled to room temperature, filtered, the insoluble material washed with 200 ml of ether and the solvents evaporated under reduced pressure. 29 g of a yellow oil are obtained which is used as it is in the following stage.

Reference： [1]Patent: US5246939,1993,A

61
[ 332-48-9 ]
[ 40064-34-4 ]
[ 147007-79-2 ]

Yield	Reaction Conditions	Operation in experiment
		A) 1-(2-(4-Fluorophenoxy)ethyl)-4-piperidone. This compound was prepared in a manner similar to example 7. From <strong>[40064-34-4]4-piperidone monohydrate hydrochloride</strong> (2.50 g, 16.3 mmol), 2-(4-fluorophenoxy)ethyl bromide (3.74 g, 17.1 mmol) there was obtained the amine as a pale yellow liquid which crystallized upon agitation (3.39 g, 88%): mp 71-73 C.; 1 H NMR (CDCl3) 2.48 (t, J=6.0 Hz, 4 H), 2.85-2.97 (m, 6 H), 4.10 (t, J=5.4 Hz, 2 H), 6.80-7.03 (m, 4 H).

Reference： [1]Patent: US6124323,2000,A

62
4-(4-fluorobenzyl)piperidine hydrobromide [ No CAS ]
[ 332-48-9 ]
4-(4-Fluorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		F) 4-(4-Fluorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride. The compound was prepared in a manner similar to example 20. From 4-(4-fluorobenzyl)piperidine hydrobromide (600 mg, 2.19 mmol) and 2-(4-fluorophenoxy)ethyl bromide (504 mg, 2.30 mmol) there was obtained the hydrochloride salt as a fluffy, colorless, crystalline solid (315 mg, 40%): mp 153-154 C.; 1 H NMR (CDCl3) 1.55-2.15 (m, 5 H), 2.50-2.83 (m, 4 H), 3.20-3.50 (m, 2 H), 3.66 (d, J=11 Hz, 2 H), 4.42-4.56 (m, 2 H), 6.76-7.12 (m, 8 H), 12.62 (bs, 1 H). Anal. Calcd for C20 H24 ClF2 NO: C, 65.30; H, 6.58; N, 3.81. Found: C, 65.08; H, 6.79; N, 3.78.

Reference： [1]Patent: US6124323,2000,A

63
4-(4-nitrobenzyl)piperidine hydrochloride [ No CAS ]
[ 332-48-9 ]
1-(2-(4-Fluorophenoxy)ethyl)-4-(4-nitrobenzyl)piperidine hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		C) 1-(2-(4-Fluorophenoxy)ethyl)-4-(4-nitrobenzyl)piperidine hydrobromide. This compound was prepared in a manner similar to example 25. From 4-(4-nitrobenzyl)piperidine hydrochloride (427 mg, 1.66 mmol) and 2-(4-fluorophenoxy)ethyl bromide (381 mg, 1.74 mmol) there was obtained the hydrobromide salt as a pale beige powder (510 mg, 94%): mp 147-148 C.; 1 H NMR (CDCl3) 1.65-1.89. (m, 3 H), 2.20 (q, J=12 Hz, 2 H), 2.69-2.90 (m, 4 H), 3.35-3.45 (m, 2 H), 3.73 (d, J=12 Hz, 2 H), 4.55 (t, J=3.6 Hz, 2 H), 6.77-7.04 (m, 4 H), 7.30 (d, J=8.4 Hz, 2 H), 8.16 (d, J=8.4 Hz, 2 H), 11.75 (bs, 1 H). Anal. Calcd for C20 H24 BrFN2 O3: C, 54.68; H, 5.51; N, 6.38. Found: C, 54.67; H, 5.36; N, 6.29.

Reference： [1]Patent: US6124323,2000,A

64
[ 4350-41-8 ]
[ 332-48-9 ]
2-(4-Chlorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)pyridinium Bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	EXAMPLE 23 2-(4-Chlorobenzyl)-1-(2-(4-fluorophenoxy)ethyl)pyridinium Bromide STR46 From a solution of 2-(4-chlorobenzyl)pyridine (500 mg, 2.45 mmol) and 2-(4-fluorophenoxy)ethyl bromide (537 mg, 2.45 mmol) in CH3 CN (5 mL) was obtained the title compound as a colorless powder (271 mg, 26%), mp 179-180 C.; 1 H NMR (CDCl3) 4.56 (t, J=4.8 Hz, 2H), 4.91 (s, 2H), 5.57 (t, J=4.8 Hz, 2H), 6.74-6.81 (m, 2H), 6.89-6.97 (m, 2H), 7.23-7.30 (m, 2H), 7.36-7.40 (m, 2H), 7.50 (dd, J=8.1 and 1.2 Hz, 1H), 7.96 (dt, J=6.9 and 1.2 Hz, 1H), 8.28 (dt, J=7.8 and 1.5 Hz, 1H), 9.31 (dd, J=6.0 and 1.2 Hz, 1H); Anal. Calcd for C20 H18 BrClFNO*H2 O: C, 54.50; H, 4.57; N, 3.18. Found: C, 54.70; H, 4.38; N, 3.14.

Reference： [1]Patent: US6124317,2000,A

65
4-(dimethylaminomethyliminomethyl)piperidine [ No CAS ]
[ 332-48-9 ]
4-aminomethyl-1-[2-(4-fluorophenoxy)ethyl]piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In toluene;	EXAMPLE 6 In a similar manner to Example 3, a mixture of 4-(dimethylaminomethyliminomethyl)piperidine (6.42 g), 2-bromoethyl 4-fluorophenyl ether (8.3 g), triethylamine (5.3 ml) and toluene (20 ml) was heated on a steam bath for 16 hours to give 4-aminomethyl-1-[2-(4-fluorophenoxy)ethyl]piperidine as an oil.

Reference： [1]Patent: US5760035,1998,A

66
[ 332-48-9 ]
[ 102308-92-9 ]
4-(2-dimethylaminoethyl)-1-[2-(4-fluorophenoxy)ethyl]piperidine dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide;	EXAMPLE 17 In a similar manner to Example 16, a mixture of 4-(2-dimethylaminoethyl)piperidine dihydrochloride (5.5 g), 2-bromoethyl 4-fluorophenyl ether (5.26 g), triethylamine (13.4 ml) and DMF (50 ml) was heated on a steam bath for 16 hours to give 4-(2-dimethylaminoethyl)-1-[2-(4-fluorophenoxy)ethyl]piperidine dihydrochloride, m.p. 260-262 C.

Reference： [1]Patent: US5760035,1998,A

67
[ 332-48-9 ]
[ 3433-37-2 ]
1-(2-(4-Fluorophenoxy)ethyl)-2-(hydroxymethyl)piperidine hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 49 1-(2-(4-Fluorophenoxy)ethyl)-2-(hydroxymethyl)piperidine hydrobromide From 2-hydroxymethylpiperidine (500 mg, 4.34 mmol) and 2-(4-fluorophenoxy)ethyl bromide (999 mg, 4.56 mmol) there was obtained a colorless oil (970 mg, 88%): 1H NMR (CDCl3) d 1.60-2.11 (m, 6 H), 2.67-3.59 (m, 6 H), 3.80 (dd, J1=11 Hz, J2=3.9 Hz, 1 H), 4.15 (dd, J, =11 Hz, J2=3.9 Hz, 1 H) 4.37-4.42 (m, 2 H), 7.13-7.35 (m, 4 H). The hydrobromide was obtained as a colorless powder (1.08 g, 96%): mp 103.5-105.5 C.; Anal. Calcd for C14H21BrFNO2: C, 50.31; H, 6.33; N, 4.19. Found: C, 50.39; H, 6.15; N, 3.99.

Reference： [1]Patent: US6218404,2001,B1

68
[ 142221-79-2 ]
[ 332-48-9 ]
4-(4-Fluorobenzoyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 80 4-(4-Fluorobenzoyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride The compound was prepared in a manner similar to example 77. From 4-(4-fluorobenzoyl)piperidine hydrobromide (1.5 g, 6.1 mmol) and 2-(4-fluorophenoxy)ethyl bromide (2.0 g, 9.2 mmol) there was obtained the free amine as a brown solid (1.0 g, 50%): mp 88-91C; 1H NMR (CDCl3) d 1.80-1.95 (m, 4H), 2.20-2.35 (m, 2H), 2.82 (t, J=6.0 Hz, 2H), 3.07 (bd, J=11.4 Hz, 2H), 3.15-3.30 (m, 1H), 4.07 (t, J=5.7 Hz, 2H), 6.80-6.90 (m, 2H), 6.96 (t, J=8.7 Hz, 2H), 7.13 (t, J=8.4 Hz, 2H), 7.96 (dd, J=5.7 and 8.4 Hz, 2H). The HCl salt was obtained as a brown solid (0.17 g, 54%): mp 138-141 C.; HRMS calcd for C20H21F2NO2 345.1540, found 345.1547.

Reference： [1]Patent: US6218404,2001,B1

69
[ 193205-24-2 ]
[ 332-48-9 ]
[ 193205-25-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile;	c) 4-(4-Chlorobenzyl)-1-(N-(2-(4-fluorophenoxy)ethyl)amino)piperidine hydrobromide. From a mixture of 1-amino-4-(4-chlorobenzyl)piperidine (500 mg, 2.22 mmol), 2-(4-fluorophenoxy)ethyl bromide (511 mg, 2.33 mmol) and K2CO3 (322 mg, 2.33 mmol) in CH3CN (10 mL) was obtained the title compound as colorless flakes (165 mg, 17%): mp 214-215 C. (dec). 1H NMR (CD3OD) 1.75-2.05 (m, 5H), 2.70 (d, J=6.9, 2H), 3.40-3.52 (m, 2H), 3.83 (d, J=13, 2H), 4.00 (t, J=4.5, 2H), 4.52 (t, J=4.5, 2H), 6.96-7.10 (m, 4H), 7.22 (d, J=8.7, 2H), 7.30 (d, J=8.7, 2H); Anal Calcd for C20H25BrClFN2O: C, 54.13; H, 5.68; N, 6.31. Found: C, 54.23; H, 5.59; N, 6.23.

Reference： [1]Patent: US6218404,2001,B1

70
[ 929193-55-5 ]
[ 332-48-9 ]
4-[2-(4-fluorophenoxy)ethoxy]-1-(2-[isopropyl(methyl)amino]-1H-benzimidazol-6-yl)pyridine-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	Example 90 4-[2-(4-fluorophenoxy)ethoxy]-1-{2-[isopropyl(methyl)amino]-1H-benzimidazol-6-yl}pyridin-2(1H)-one Potassium carbonate (60 mg) and 1-(2-bromoethoxy)-4-fluorobenzene (60 mg) were added to a DMF solution (5 mL) of the compound (60 mg) obtained in Production Example 41-2, and stirred overnight at room temperature. Ethyl acetate was added to the reaction liquid, washed successively with water and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (NH silica gel, chloroform) to obtain the entitled compound (14.6 mg). 1H-NMR (400 MHz, DMSO-d6, delta ppm): 1.17 (6H, d, J=6.7 Hz), 2.90 (3H, s), 4.29-4.35 (4H, m), 4.49 (1H, septet, J=6.7 Hz), 5.92 (1H, d, J=2.7 Hz), 6.03 (1H, dd, J=7.6 Hz, 2.7 Hz), 6.79 (1H, brs), 6.99-7.05 (3H, m), 7.11-7.19 (3H, m), 7.52 (1H, d, J=7.4 Hz), 11.32 (1H, brs). ESI-MS Found: m/z 437 [M+H]+

Reference： [1]Patent: US2009/264426,2009,A1 .Location in patent: Page/Page column 65
[2]Patent: WO2007/29847,2007,A1 .Location in patent: Page/Page column 133

71
[ 910114-60-2 ]
[ 332-48-9 ]
[ 1353585-37-1 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetonitrile; at 20℃; for 16h;	To a reaction vessel containing compound 8c (28 mg, 0.1 mmol) in acetonitrile (0.5 mL) was added cesium carbonate (32 mg, 0.1 mmol) and 1-(2-bromo-ethoxy)-4-fluoro-benzene (17.1 mg, 0.1 mmol). The mixture was stirred at room temperature for 16 h, then concentrated. The residue was taken up in dichloromethane/water, absorbed onto diatomaceous earth, and eluted with dichloromethane. The eluate was concentrated to provide compound 17a.
	With caesium carbonate; In acetonitrile; at 20℃; for 16h;	To a reaction vessel containing compound 8c (28 mg, 0.1 mmol) in acetonitrile (0.5 ml.) was added cesium carbonate (32 mg, 0.1 mmol) and 1-(2-bromo-ethoxy)-4-fluoro-benzene (17.1 mg, 0.1 mmol). The mixture was stirred at room temperature for 16 h, then <n="111"/>concentrated. The residue was taken up in dichloromethane/water, absorbed onto diatomaceous earth, and eluted with dichloromethane. The elupsilonate was concentrated to provide compound 17a.
	With caesium carbonate; In acetonitrile; at 20℃; for 16h;	To a reaction vessel containing compound 8c (28 mg, 0.1 mmol) in acetonitrile (0.5 mL) was added cesium carbonate (32 mg, 0.1 mmol) and 1-(2-bromo-ethoxy)-4-fluoro-benzene (17.1 mg, 0.1 mmol). The mixture was stirred at room temperature for 16 h, then concentrated. The residue was taken up in dichloromethane/water, absorbed onto diatomaceous earth, and eluted with dichloromethane. The eluate was concentrated to provide compound 17a.

Reference： [1]Patent: US2008/269225,2008,A1 .Location in patent: Page/Page column 40
[2]Patent: WO2007/79214,2007,A2 .Location in patent: Page/Page column 107-108
[3]Patent: US2011/319400,2011,A1 .Location in patent: Page/Page column 39

72
[ 332-48-9 ]
[ 82799-14-2 ]
[ 362657-45-2 ]

Yield	Reaction Conditions	Operation in experiment
44%	With K2CO3; In 2-Methylpentane; ethyl acetate; N,N-dimethyl-formamide;	Step 1. 5-[2-(4-fluoro-phenoxy)-ethoxy]-tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-13-one A mixture of 2-hydroxy-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[a][8]annulen-11-one (21.7 g; J. Org. Chem 1982, 47, 4329), K2CO3 (17.7 g) and 1-(2-Bromo-ethoxy)-4-fluoro-benzene (40.3 g) in DMF (400 ml) were stirred for 72 hours at 120 C. The reaction was then cooled to room temperature and the solvent removed in vacuo. The residue was then washed with saturated NaHCO3 solution and the organics extracted with EtOAc (3*200 ml). The organics were then combined, dried (MgSO4) and the solvent removed in vacuo yielding a dark brown oil which was purified by flash chromatography on silica eluding 20% EtOAc in isohexane giving the title alkylated ketone (15.97 g, 44%). MS (ES+) 341 [M+H]+.

Reference： [1]Patent: US2004/29862,2004,A1

73
[ 1034981-48-0 ]
[ 332-48-9 ]
[ 1034981-49-1 ]
[ 1034981-50-4 ]

Yield	Reaction Conditions	Operation in experiment
14%; 7%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 17h;	EXAMPLE 7Synthesis of 2-(2-(2-(4-fluorophenoxy)ethyl)-2/T-tetrazol-5-yl)-4-methyl-J/V-(pyridin-3-ylmethyl)thiazole-5-carboxamide and 2-(l-(2-(4-fluorophenoxy)ethyl)-l£-r-tetrazol-5-yl)-4-methyl-lambdaf-(pyridin-3-ylmethyl)thiazole-5-carboxamideTo a mixture of 4-methyl-lambdar-(pyridin-3-ylmethyl)-2-(2//-tetrazol-5-yl)thiazole-5- carboxamide (0.10 g, 0.33 mmol) and potassium carbonate (0.069 g, 0.50 mmol) in NJV- dimethylformamide (2 mL) was added l-(2-bromoethoxy)-4-fluorobenzene (0.08 mL, 0.37 mmol). The reaction mixture was stirred at ambient temperature for 17 hours, diluted with ethyl acetate (15 mL) and washed with brine (5 mL). The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate). Compound 2-(l-(2-(4- fluorophenoxy)ethyl)-lH-tetrazol-5-yl)-4-methyl-lambdar-(pyridin-3-ylmethyl)thiazole-5- carboxamide was first eluted from the column and isolated as a white solid (0.010 g, 7%): 1H NMR (300 MHz, CDCl3) delta 8.61-8.55 (m, 2H), 7.77-7.68 (m, IH), 7.37-7.28 (m, IH), 7.03-6.88 (m, 2H), 6.86-6.74 (m, 2H), 6.49 (t, J= 5.8 Hz, IH), 5.06 (t,J= 5.3 Hz, 2H), 4.65 (d, J= 5.8 Hz, 2H), 4.55 (t, J= 5.3 Hz, 2H), 2.79 (s, 3H); MS (ES+) m/z 440.3 (M + 1 ). Compound 2-(2-(2-(4-fluorophenoxy)ethyl)-2H-tetrazol-5-yl)-4-methyl-N-(pyridin-3- ylmethyl)thiazole-5-carboxamide was second eluted from the column and isolated as a white solid (0.02 g, 14%): mp 137-138 0C (ethyl acetate); 1H NMR (300 MHz, CDCl3) delta 8.59 (br s, IH), 8.54 (br s, IH), 7.76-7.65 (m, IH), 7.35-7.26 (m, IH), 6.94-6.86 (m, 2H), <n="97"/>6.72-6.66 (m, 2H), 6.58 (t, J= 5.8 Hz, IH), 5.31 (t, J= 5.4 Hz, 2H), 4.64 (d, J= 5.8 Hz, 2H), 4.45 (t,J= 5.4 Hz, 2H), 2.72 (s, 3H); 13C NMR (75 MHz, CDCl3) delta 161.3, 160.2, 157.8, 157.2, 153.8, 153.7, 153.7, 149.2, 149.2, 135.8, 127.7, 116.2, 115.9, 115.8, 65.6, 53.0, 41.8, 17.5; MS (ES+) m/z 440.3 (M + 1).

Reference： [1]Patent: WO2008/74835,2008,A1 .Location in patent: Page/Page column 95-96

74
6-methoxy-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-pyrrolidine] [ No CAS ]
[ 332-48-9 ]
1'-[2-(4-fluorophenoxy)ethyl]-6-methoxy-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-pyrrolidine] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 50℃;	6-Methoxy-2,3, 4,9-tetrahydrospiro [beta-carboline-1,3'-pyrrolidine] (COMPARATIVE EXAMPLE 182,30. 0 mg, 0.12 mmol) was suspended in DMSO(200 L) and DIPEA(114L, 0.65 mmol) was added.1- (2-Bromoethoxy)-4-fluorobenzene (26.8 mg, 0.12 mmol) in DMSO (400 L) was added and the solution was stirred at50 C overnight. The reaction mixture was diluted with water and extracted one time with EtOAc. The organic phase was dried overNa2S04, filtered and the solvent was removed at reduced pressure and the remaining oil was then diluted with MeCN(1 mL) and purified by direct injection to a preparative HPLC/UV System, MeCN : H20 (0.1% TFA) 22-43% giving a yellow oil 16 mg, 26%. HPLC 97%,Rr1. 644 min (System A. 10-97% MeCN), 95%,R-r-1. 477 min (System B. 10-97% MeCN). 'H NMR (400 MHz,MeOD) 8 ppm 2.64-2. 71(m,1 H) 2.75-2. 82(m,1 H) 3.06 (t,J=6. 1 Hz, 2 H) 3.57-3. 79(m, 7 H) 3.81 (s, 3 H) 4.05 (d, J=12.9 Hz, 1 H) 4.32(t,J=4. 9 Hz, 2 H) 6.86 (dd,J=8. 8,2. 4 Hz,1 H) 6.97-7. 04(m,5 H) 7.27 (d, J=8. 8 Hz,1 H) MS (ESI+)m/z 396 (M+H)+.

Reference： [1]Patent: WO2005/48916,2005,A2 .Location in patent: Page/Page column 72

75
[ 64-18-6 ]
[ 1026791-31-0 ]
[ 332-48-9 ]
[ 1196091-16-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 26 (R)-1-[2-(4-Fluoro-phenoxy)-ethyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane formate A mixture of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Example 14e) (50 mg) and 1-(2-bromoethoxy)-4-fluorobenzene (50 mg) in acetonitrile (1 mL) was stirred at room temperature for 22 h. Purification by prep. HPLC using 5-98% MeCN/H2O containing 0.1% formic acid gave the title compound (19 mg) as a colourless oil. m/e 466 [M]+ 1H NMR (400 MHz, DMSO-D6): delta 8.39 (s, 1H), 7.28-7.23 (m, 4H), 7.20-7.11 (m, 3H), 6.97-6.92 (m, 2H), 5.06-4.99 (m, 1H), 4.39-4.28 (m, 2H), 3.93 (ddd, 1H), 3.70-3.56 (m, 2H), 3.56-3.46 (m, 4H), 3.15-3.03 (m, 1H), 2.35-2.20 (m, 2H), 2.15-2.03 (m, 2H), 1.97 -1.78 (m, 3H), 1.73-1.61 (m, 1H), 1.61-1.39 (m, 9H).
		Example 26: (R)-l-[2-(4-Fluoro-phenoxy)-ethyl]-3-(l-phenyI- cycloheptanecarbonyloxy)-l-azonia-bicyclo[2.2.2]octane formate HA mixture of 1 -phenyl-cycloheptanecarboxylic acid (7?)-(l-aza-bicyclo[2.2.2]oct-3-yl) ester (Example 14e) (50 mg) and l-(2-bromoethoxy)-4-fluorobenzene (50 mg) in acetonitrile (1 mL) was stirred at room temperature for 22h. Purification by prep. HPL using 5-98% MeCN/H2O containing 0.1% formic acid gave the title compound (19 mj a colourless oil.m/e 466 [M]+ 1H NMR (400 MHz, DMSO-D6): delta 8.39 (s, IH), 7.28-7.23 (m, 4H), 7.20-7.11 (m, 3P 6.97-6.92 (m, 2H), 5.06-4.99 (m, IH), 4.39-4.28 (m, 2H), 3.93 (ddd, IH), 3.70-3.56 2H), 3.56-3.46 (m, 4H), 3.15-3.03 (m, IH), 2.35-2.20 (m, 2H), 2.15-2.03 (m, 2H), 1.78 (m, 3H), 1.73-1.61 (m, IH), 1.61-1.39 (m, 9H).

Reference： [1]Patent: US2011/172237,2011,A1 .Location in patent: Page/Page column 28
[2]Patent: WO2009/138707,2009,A1 .Location in patent: Page/Page column 74

76
[ 31696-00-1 ]
[ 332-48-9 ]
[ 863566-36-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of diethyl but-3-en-1-ylmalonate (2.00 g, 9.3 mmol) in DMF was added NaH (448.0 mg, 11.2 mmol) at 0 C. The mixture was stirred at 0 C for 30 min. Then 1- (2- bromoethoxy) -4-fluorobenzene was added and the mixture was stirred at room temperature for 10.5 hr. The reaction mixture was quenched with water and the mixture was extracted with AcOEt. The organic layer was dried over Na2S04, filtered and evaporated. The crude product was purified by silica gel column chromatography (hexane: AcOEt = 200: 1 to 20: 1) to give the titled compound (2.2 g). 'H NMR (CDC13) 8 : 7.00-6. 90 (m, 2H), 6.80-6. 76 (m, 2H), 5. 85-5. 67 (m, 1H), 5.07-4. 96 (m, 2H), 4.30-4. 20 (m, 4H), 4.05-3. 95 (m, 2H), 2.45-2. 40 (m, 2H), 2.15-1. 92 (m, 4H), 1.29-1. 15 (m, 6H) ppm.

Reference： [1]Patent: WO2005/80317,2005,A2 .Location in patent: Page/Page column 187

77
[ 1189785-20-3 ]
[ 332-48-9 ]
[ 76-05-1 ]
5-[2-(4-fluorophenoxy)ethyl]-2,11-dimethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A flask containing tetrahydrofuran (5.0 niL) was charged with sodium amide (109 mg, 2.65 mmol; Alfa Aesar), chilled to 0 0C, and treated with 2,1 l-dimethyl-5,6,7,8,9,10- hexahydro-7,10-epiminocyclohepta[delta]indole (300 mg, 1.326 mmol; Example IA), added in portions. After 5 minutes, the ice bath was removed and the mixture was heated to 60 0C for 15 minutes. The solution was cooled to room temperature and l-(2-bromoethoxy)-4- fluorobenzene (348 mg, 1.591 mmol; Aldrich) was added slowly. The reaction mixture was stirred overnight at room temperature, then diluted with water (5 mL) and extracted with dichloromethane (2x10 mL). The combined organic extracts were dried over magnesium sulfate, filtered, concentrated in vacuo, and the resulting residue was purified by reverse- phase HPLC (Phenomenex Luna C8(2) 5 mum IOOA AXIA column, 30x75 mm, 10-95% gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid, flow rate 50 mL/minute) to afford the title compound as the trifluoroacetic acid salt: 1H NMR (300 MHz, methanol-^) delta ppm 1.79 - 2.07 (m, 1 H), 2.12 - 2.30 (m, 1 H), 2.34 - 2.50 (m, 4 H), 2.50 - 2.66 (m, 1 H), 2.93 (s, 3 H), 3.02 - 3.20 (m, 1 H), 3.66 (d, J=17.1 Hz, 1 H), 4.13 - 4.37 (m, 3 H), 4.42 - 4.58 (m, 2 H), 4.93 - 5.12 (m, 1 H), 6.61 - 6.84 (m, 2 H), 6.81 - 7.01 (m, 2 H), 7.01 - 7.14 (m, 1 H), 7.31 (s, 1 H), 7.34 - 7.43 (m, 1 H); MS (ESI) m/z 365 (M+H)+.

Reference： [1]Patent: WO2010/36998,2010,A2 .Location in patent: Page/Page column 128-129

78
[ 1079893-01-8 ]
[ 332-48-9 ]
[ 1250254-97-7 ]

Reference： [1]Journal of Chemical Research,2010,p. 71 - 74

79
[ 1207950-11-5 ]
[ 332-48-9 ]
[ 1250254-98-8 ]

Reference： [1]Journal of Chemical Research,2010,p. 71 - 74

80
[ 332-48-9 ]
[ 40064-34-4 ]
4-(4-Chloroanilino)-1-(2-(4-fluorophenoxy)ethyl)piperidine dihydrochloride [ No CAS ]

Reference： [1]Patent: US6124323,2000,A

81
N-ethylcyclohexylamine hydrochloride [ No CAS ]
[ 332-48-9 ]
N-ethyl-N-[2-(4-fluorophenoxy)ethyl]cyclohexylamine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%		1-(2-Bromoethoxy)-4-fluorobenzene (25.5 g (0.116 mol)) and N-ethylcyclohexylamine hydrochloride (28.5 g (0.174 mol)) were dissolved in ethanol (400 mL), and then potassium carbonate (48.7 g (0.35 mol)) and sodium iodide (44.1 g (0.232 mol)) were added to the solution. The mixture was stirred for 48 hours under heating at reflux, and the reaction mixture was returned to room temperature. The insoluble fraction was removed by filtration and the solvent was distilled away under reduced pressure. The residue was purified by a silica gel chromatography (petroleum ether: ethyl acetate = 6 : 1) and hydrogen chloride gas was passed into the resulting oil to precipitate a crystal, which was collected by filtration to obtain the target N-ethyl-N-[2-(4-fluorophenoxy)ethyl]cyclohexylamine hydrochloride (5.3 g, 17.6 mmol, yield 24%).

Reference： [1]Patent: EP2357165,2011,A1 .Location in patent: Page/Page column 18-19

82
[ 332-48-9 ]
[ 5550-12-9 ]
[ 76-05-1 ]
7-(2-(4-fluorophenoxy)ethyl)guanosine-5'-monophosphate trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3837 - 3851

83
[ 55104-32-0 ]
[ 332-48-9 ]
[ 1424363-43-8 ]

Yield	Reaction Conditions	Operation in experiment
38%		General procedure: 6-Hydroxyphthalide (9) (0.33 mmol) was dissolved in N,N-dimethylformamide (DMF; 3 mL) and stirred over K2CO3 (1.14 mmol) for 5 min. The appropriately substituted alkyl bromide (0.37 mmol) was added and the reaction mixture was stirred for 12 h at 50-100 ºC. The K2CO3 was removed by filtration and the reaction mixture was dried in a stream of air. The resulting residue was recrystallized from ethanol to yield the C6-substituted phthalide analogues 6a-r.1 Benzylaminophthalide (6s) was synthesized according to the same procedure from 6-aminophthalide (8) and benzyl bromide

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1269 - 1273

84
C₁₆H₂₀N₃O₂PolS [ No CAS ]
[ 332-48-9 ]
C₂₄H₂₇FN₃O₃PolS [ No CAS ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 180 - 188

85
C₁₆H₂₀N₃O₂PolS [ No CAS ]
[ 332-48-9 ]
C₂₄H₂₇FN₃O₃PolS [ No CAS ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 180 - 188

86
[ 894357-92-7 ]
[ 332-48-9 ]
[ 1428870-11-4 ]

Reference： [1]Russian Chemical Bulletin,2012,vol. 61,p. 1161 - 1168
Izv. Akad. Nauk, Ser. Khim.,2012,p. 1150 - 1157

87
[ 1187020-26-3 ]
[ 332-48-9 ]
[ 1404059-56-8 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 2633 - 2644

88
[ 332-48-9 ]
[ 34950-82-8 ]
C₁₅H₁₄BrFN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1-Dimethylurea; sodium hydride; In mineral oil; at 0 - 22℃; for 5h;	DMA (3 mL) within at F1 (100 mg, 0.456 mmol) stirring a solution in NaH (mineral oil in 22 mg, 0.56 mmol, 60% dispersion) to 0 C in 0.5 sigan during the addition, and then the 1-(2-bromoethoxy)-4-fluorobenzene was added (122 mg, 0.56 mmol), the mixture was stirred at 0 C for 1 hour and further stirred for 4 hours at 22 C. After stopping the reaction with water (20 mL), then extracted with EtOAc (15 mL × 3), washed with brine (15 mL × 2) and concentrated under dried under reduced pressure over anhydrous Na2SO4, the residue was prep -TLC (PE / EtOAc = 3: 1) was produced and purified by the F2.

Reference： [1]Patent: KR101576386,2015,B1 .Location in patent: Paragraph 0158; 0161-0162

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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
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
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.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
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.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
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
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
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

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 332-48-9 ] {[proInfo.proName]}

Quality Control of [ 332-48-9 ]

Related Doc. of [ 332-48-9 ]

Product Details of [ 332-48-9 ]

Calculated chemistry of [ 332-48-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 332-48-9 ]

Application In Synthesis of [ 332-48-9 ]

[ 332-48-9 ] Synthesis Path-Upstream 1~1

[ 332-48-9 ] Synthesis Path-Downstream 1~88

Pharmaceutical Intermediates of [ 332-48-9 ]

Sorbinil Intermediates

Related Functional Groups of [ 332-48-9 ]

Fluorinated Building Blocks

Aryls

Bromides

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 332-48-9 ]

Related Functional Groups of
[ 332-48-9 ]