Potassium Carbonate → 1-[2-(4-Hydroxy-3-methylphenoxy)ethyl]-4-(4-fluorobenzyl)piperidine hydrochloride
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.C([O:23][C:24]1[CH:33]=[CH:32][C:27]([O:28][CH2:29][CH2:30]Br)=[CH:26][C:25]=1[CH3:34])C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>>[ClH:1].[OH:23][C:24]1[CH:33]=[CH:32][C:27]([O:28][CH2:29][CH2:30][N:11]2[CH2:10][CH2:9][CH:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([F:2])=[CH:15][CH:14]=3)[CH2:13][CH2:12]2)=[CH:26][C:25]=1[CH3:34]Participants
4
Procedure
The title compound was prepared from 4-(4-fluorobenzyl)piperidine hydrochloride (344 mg, 1.5 mmol), 2-(4-benzoxy-3-methylphenoxy)ethyl bromide (482 mg, 1.5 mmol) and potassium carbonate (518 mg, 3.8 mmol) in two steps as white-off solid (240 mg): mp 118-120° C. 1H NMR (CD3OD) 1.40 (m, 2 H), 1.699 (m, 3 H), 1.975 (s, 3 H), 2.441 (t, 2 H), 2.82 (m, 2 H), 3.310 (m, 2 H), 3.45 (m, 2 H), 4.054 (s, 2 H), 6.481 (s, 2 H), 6.753 (s, 1 H), 6.83 (m, 2 H), 7.021 (m, 2 H). Anal. Calcd for C21H27ClFNO2.0.7H2O: C, 64.25; H, 7.29; N, 3.57. Found: C, 64.24; H, 7.02; N, 3.91.
Sources & evidence
- ORD record
- ord-3442918bb2db4788b2f155702412c806
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124323
Reaction notes
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