Potassium Carbonate → 4-(2-Fluoro-4-methylbenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride

HRID 1955199Notes

Reaction equation

HRID 1955199 reaction equation
[ClH:1].[F:2][C:3]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:4]=1[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[F:17][C:18]1[CH:27]=[CH:26][C:21]([O:22][CH2:23][CH2:24]Br)=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>>[ClH:1].[F:2][C:3]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:4]=1[CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:24][CH2:23][O:22][C:21]2[CH:26]=[CH:27][C:18]([F:17])=[CH:19][CH:20]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 20641711-(2-Bromoethoxy)-4-fluorobenzeneHCID 232943474-(2-Fluoro-4-methylbenzyl)piperidine hydrochloride

Product 1

HCID 232944874-(2-Fluoro-4-methylbenzyl)-1-(2-(4-fluorophenoxy)ethyl)piperidine hydrochloride

Procedure

The title compound was prepared from 4-(2-fluoro-4-methylbenzyl)piperidine hydrochloride (375 mg, 1.54 mmol), 2-(4-fluorophenoxy)ethyl bromide (355 mg, 1.62 mmol) and K2CO3 (437 mg, 3.16 mmol) as a colorless crystalline solid (362 mg), mp 167-168° C.; 1H NMR (CDCl3) 1.60-1.80 (m, 3H), 1.95-2.15 (m, 2H), 2.30 (s, 3H), 2.61 (d, J=6.6 Hz, 2H), 2.65-2.83 (m, 2H), 3.20-3.70 (m, 4H), 4.51 (d, J=4.2 Hz, 2H), 6.78-7.00 (m, 7H), 12.60 (bs, 1H); Anal. Calcd for C21H26ClF2NO: C, 66.05; H, 6.86; N, 3.67. Found: C, 66.09; H, 6.78; N, 3.46.

Sources & evidence

ORD record
ord-3f915d9cfbf543daabe595f5cc4f9062
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

Loading…