Potassium Carbonate → 4-(4-Fluorobenzyl)-1-[2-(2-hydroxyphenoxy)ethyl]piperidine hydrochloride

HRID 1955221Notes

Reaction equation

HRID 1955221 reaction equation
[ClH:1].[F:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[CH2:16]([O:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[O:26]CCBr)[C:17]1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>>[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]2[CH2:9][CH2:10][N:11]([CH2:17][CH2:16][O:23][C:24]3[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=3[OH:26])[CH2:12][CH2:13]2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 170394924-[(4-Fluorophenyl)methyl]piperidine hydrochlorideHCID 232945431-Benzyloxy-2-(2-bromoethoxy)benzene

Product 1

HCID 232944084-(4-Fluorobenzyl)-1-[2-(2-hydroxyphenoxy)ethyl]piperidine hydrochloride

Procedure

The title compound was prepared from 4-(4-fluorobenzyl)piperidine hydrochloride (298 mg, 1.30 mmol), 2-(2-benzyloxyphenoxy)ethyl bromide (399 mg, 1.3 mmol) and potassium carbonate (449 mg, 3.2 mmol) in two steps as white-off solid (240 mg): mp 233-235° C. (dec.). 1H NMR (CD3OD) 1.532 (m, 2 H), 1.848 (d, J=13.2 Hz, 3 H), 2.571 (d, J=6.3 Hz, 2 H), 3.0 (m, 2 H), 3.483 (m, 2 H), 3.603 (d, J=10.5 Hz, 2 H), 4.262 (t, J=5.1 Hz, 2 H), 6.752-6.825 (m, 3 H), 6.909-6.986 (m, 3 H), 7.126-7.173 (m, 2 H).

Sources & evidence

ORD record
ord-d74b20c845ee444fae33ff7cfb709dfd
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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