Potassium Carbonate → 4-(4-Fluorobenzyl)-1-[2-(3-Hydroxyphenoxy)ethyl]piperidine hydrochloride

HRID 1955222Notes

Reaction equation

HRID 1955222 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:25]=[C:26]([CH:31]=[CH:32][CH:33]=1)[O:27]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]=[C:26]([OH:27])[CH:25]=3)[CH2:12][CH2:13]2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 170394924-[(4-Fluorophenyl)methyl]piperidine hydrochlorideHCID 232945632-(3-Benzyloxyphenoxy)ethyl bromide

Product 1

HCID 232942924-(4-Fluorobenzyl)-1-[2-(3-Hydroxyphenoxy)ethyl]piperidine hydrochloride

Procedure

The title compound was prepared from 4-(4-fluorobenzyl)piperidine hydrochloride (298 mg, 1.30 mmol), 2-(3-benzyloxyphenoxy)ethyl bromide (399 mg, 1.3 mmol) and potassium carbonate (449 mg, 3.2 mmol) in two steps as white-off solid (250 mg): mp 145-147° C. 1H NMR (CD3OD) 1.529 (m, 2 H), 1.821 (d, J=12.9 Hz, 2 H), 2.551 (d, J=6.3 Hz, 2 H), 3.003 (m, 2 H), 3.468 (m, 2 H), 3.541 (m, 2 H), 4.243 (t, J=5.4 Hz, 2 H), 6.369-6.422 (m, 3 H), 6.924-7.034 (m, 3 H), 7.120-7.167 (m, 2 H).

Sources & evidence

ORD record
ord-dc9ccaa8b96549d498824b15609fe861
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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