Potassium Carbonate → 1-[2-(4-Hydroxy-3-methylphenoxy)ethyl]-4-hydroxy-4-(4-methylbenzyl)piperidine hydrochloride
Reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15]Br)=[CH:11][C:10]=1[CH3:19])C1C=CC=CC=1.[ClH:20].[CH2:21]([C:23]1[CH:36]=[CH:35][C:26]([CH2:27][C:28]2([OH:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:25][CH:24]=1)C.C(=O)([O-])[O-].[K+].[K+]>>[ClH:20].[OH:8][C:9]1[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][N:31]2[CH2:32][CH2:33][C:28]([OH:34])([CH2:27][C:26]3[CH:35]=[CH:36][C:23]([CH3:21])=[CH:24][CH:25]=3)[CH2:29][CH2:30]2)=[CH:11][C:10]=1[CH3:19]Participants
4
Procedure
The title compound was prepared from 2-(4-benzyloxy-3-methylphenoxy)ethyl bromide (385 mg, 1.2 mmol), 4-(4-ethylbenzyl)-4-hydroxypiperidine hydrochloride (290 g, 1.2 mmol) and potassium carbonate (414 mg, 3 mmol) in two steps as white solid (200 mg): mp 90-94° C. (dec.). 1H NMR (CD3OD) 1.641 (m, 2 H), 1.859 (m, 2 H), 2.083 (5, 3 H), 2.224 (s, 3 H), 2.718 (s, 2 H), 3.260-3.423 (m, 6 H), 4.133 (m, 2 H), 6.585 (s, 2 H), 6.668 (s, 1 H), 7.035 (m, 4 H).
Sources & evidence
- ORD record
- ord-eb14d343d8614fe48eb533172b6e5607
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124323
Reaction notes
Loading…