Potassium Carbonate → 1-[2-(4-Hydroxy-3-methylphenoxy)ethyl]-4-(2-fluoro-4-methylbenzyl)piperidine hydrochloride
Reaction equation
[ClH:1].[F:2][C:3]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:4]=1[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C([O:24][C:25]1[CH:34]=[CH:33][C:28]([O:29][CH2:30][CH2:31]Br)=[CH:27][C:26]=1[CH3:35])C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>>[ClH:1].[OH:24][C:25]1[CH:34]=[CH:33][C:28]([O:29][CH2:30][CH2:31][N:9]2[CH2:8][CH2:7][CH:6]([CH2:5][C:4]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:3]=3[F:2])[CH2:11][CH2:10]2)=[CH:27][C:26]=1[CH3:35]Participants
4
Procedure
The title compound was prepared from 4-(2-fluoro-4-methylbenzyl)piperidine hydrochloride (311.7 mg, 1.28 mmol), 2-(4-benzyloxy-3-methylphenoxy)ethyl bromide (411 mg, 1.28 mmol) and potassium carbonate (444 mg, 3.2 mmol) in two steps as white-off solid (244 mg), mp 165-167° C. 1H NMR (CD3OD) 1.503 (m, 2 H), 1.848 (m, 3 H), 2.076 (s, 3 H), 2.223 (s, 3 H), 2.560 (m, 2 H), 2.932 (m, 2 H), 3.389 (m, 2 H), 3.526 (m, 2 H), 4.141 (t, J=5.1 Hz, 2 H), 6.758 (s, 1 H), 6.667 (s, 1 H), 6.788-6.858 (m, 3 H), 7.109 (m, 1 H). Anal. Calcd for C22H29ClFNO2 : C, 67.08; H, 7.42; N, 3.98. Found: C, 66.85; H, 7.44; N, 3.46.
Sources & evidence
- ORD record
- ord-89f2d82ec3504051890b629c3b7c8f53
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124323
Reaction notes
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