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

HRID 1955203Notes

Reaction equation

HRID 1955203 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]=[C:26]([F:28])[CH:25]=[CH:24][C:19]=1[O:20][CH2:21][CH2:22]Br.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]([CH2:22][CH2:21][O:20][C:19]2[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:18]=2[F:17])[CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 232942611-(2-Bromoethoxy)-2,4-difluorobenzeneHCID 232943474-(2-Fluoro-4-methylbenzyl)piperidine hydrochloride

Product 1

HCID 232943784-(2-Fluoro-4-methylbenzyl)-1-(2-(2,4-difluorophenoxy)ethyl)piperidine hydrochloride

Procedure

The title compound was prepared from 4-(2-fluoro-4-methylbenzyl)piperidine hydrochloride (300 mg, 1.23 mmol), 2-(2,4-difluorophenoxy)ethyl bromide (321 mg, 1.35 mmol) and K2CO3 (357 mg, 2.58 mmol) as colorless flakes (326 mg): mp 180-182° C.; 1H NMR (CDCl3) 1.65-1.90 (m, 3H), 1.95-2.13 (m, 2H), 2.30 (s, 3H), 2.61 (d, J=6.9 Hz, 2H), 2.65-2.87 (m, 2H), 3.30-3.55 (m, 2H), 3.69 (d, J=12 Hz, 2H), 4.59 (t, J=4.2 Hz, 2H), 6.75-7.02 (m, 6H), 12.61 (bs, 1H); Anal Calcd. for C21H,25ClF3NO: C, 63.08; H, 6.30; N, 3.50. Found: C, 62.94; H, 6.34; N, 3.36.

Sources & evidence

ORD record
ord-448bf223febe4822a561730f746b1ba4
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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