Potassium Carbonate → 1-[2-(4-Hydroxyphenoxy)ethyl]-4-(2-fluorobenzyl)piperidine hydrochloride

HRID 1955197Notes

Reaction equation

C([O:8][C:9]1[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15]Br)=[CH:11][CH:10]=1)C1C=CC=CC=1.[ClH:19].[F:20][C:21]1[CH:33]=[CH:32][CH:31]=[CH:30][C:22]=1[CH2:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>>[ClH:19].[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][N:27]2[CH2:28][CH2:29][CH:24]([CH2:23][C:22]3[CH:30]=[CH:31][CH:32]=[CH:33][C:21]=3[F:20])[CH2:25][CH2:26]2)=[CH:17][CH:18]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 107570881-(Benzyloxy)-4-(2-bromoethoxy)benzene

HCID 46172843193357-26-5

Product 1

HCID 232943651-[2-(4-Hydroxyphenoxy)ethyl]-4-(2-fluorobenzyl)piperidine hydrochloride

Procedure

The title compound was prepared from 2-(4-benzyloxyphenoxy)ethyl bromide (0.393 g, 1.28 mmol), 4-(2-fluorobenzyl)piperidine hydrochloride (0.294 g, 1.28 mmol) and potassium carbonate (0.442 g, 3.2 mmol) in two steps as an off white solid (0.237 g), mp 196-198° C. 1H NMR (CD3OD) 1.629 (m, 2 H), 1.900 (m, 3 H), 2.704 (m, 2 H), 3.052 (m, 2 H), 3.500 (m, 2 H), 3.612 (m, 2 H), 4.252 (m, 2 H), 6.703 (d, J=9. 0 Hz, 2 H), 6.825 (6, J=9.0 Hz, 2 H), 7.057-7.248 (m, 2 H), 7.248 (m, 2 H). Anal. Calcd for C20H25ClFNO2.1.2H2O: C, 61.70; H, 7.15; N, 3.60. Found: C, 61.45; H, 6.90; N, 3.53.

Sources & evidence

ORD record: ord-3c0afbf68b8d4fe8b76e53899881951a
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124323

Reaction notes

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