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

HRID 1955224Notes

Reaction equation

HRID 1955224 reaction equation
[ClH:1].[CH3:2][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].[OH:26][C:25]1[CH:30]=[CH:31][CH:32]=[CH:33][C:24]=1[O:23][CH2:16][CH2:17][N:11]1[CH2:12][CH2:13][CH:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([CH3:2])=[CH:15][CH:14]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 232942754-(4-Methylbenzyl)piperidine hydrochlorideHCID 232945431-Benzyloxy-2-(2-bromoethoxy)benzene

Product 1

HCID 232943951-[2-(2-Hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochloride

Procedure

The title compound was prepared from 4-(4-methylbenzyl)piperidine hydrochloride (294 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 225-227° C. 1H NMR (CD3OD) 1.436 (m, 2 H), 1.758 (d, J=12.9 Hz, 3 H), 2.135 (s, 3 H), 2.443 (d, J=6.3 Hz, 2 H), 2.900 (m, 2 H), 3.388 (m, 2 H), 3.503 (m, 2 H), 4.172 (t, J=5.7 Hz, 2 H), 6.651-6.739 (m, 3 H), 6.818 (m, 1 H), 6.928 (m, 4 H).

Sources & evidence

ORD record
ord-51f7e709b272447093a4eec3fbead0fb
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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