Potassium Carbonate → 1-[2-(4-Hydroxy-3-methylphenoxy)ethyl]-4-(4-methylbenzyl)piperidine hydrochloride
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.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[CH2:12][CH2:13][CH:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([CH3:2])=[CH:15][CH:14]=3)[CH2:9][CH2:10]2)=[CH:26][C:25]=1[CH3:34]Participants
4
Procedure
The title compound was prepared from 4-(4-methylbenzyl)piperidine hydrochloride (339 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 (250 mg): mp 161-163° C. 1H NMR (CD3OD) 1.328 (m, 2 H), 1.697 (m, 3 H), 1.964 (s, 3 H), 2.092 (s, 3 H), 2.384 (m, 2 H), 2.826 (m, 2 H), 3.279 (m, 2 H), 3.427 (m, 2 H), 4.037 (d, J=4.5 Hz, 2 H), 6.469 (m, 2 H), 6.563 (m, 1 H), 6.877 (m, 4 H). Anal. Calcd for C22H30ClNO2.0.6H2O: C, 68.31; H, 8.13; N, 3.62. Found: C, 68.52; H, 7.85; N, 3.65.
Sources & evidence
- ORD record
- ord-59f4a9cb298045cba664cd3ebb057cc9
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124323
Reaction notes
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