Potassium Carbonate → 1-[2-(4-Hydroxy-3-fluorophenoxy)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[F: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[F: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-benzoxy-3-fluorophenoxy)ethyl bromide (411 mg, 1.28 mmol), potassium carbonate (444 mg, 3.2 mmol) in two steps as white-off solid (270 mg), mp 128-130° C. 1H NMR (CD3OD) 1.40 (m, 2 H), 1.704 (m, 3 H), 2.114 (s, 3 H), 2.422 (d, J=6.3 Hz, 2 H), 2.837 (m, 2 H), 3.303 (m, 2 H), 3.430 (d, J=11.4 Hz, 2 H), 4.072 (m, 2 H), 6.50 (m, 1 H), 6.632-6.750 (m, 4 H), 6.90 (m, 1 H). Anal. Calcd for C21H26ClF2NO2.0.4H2O: C, 62.25; H, 6.67; N, 3.46. Found: C, 62.20; H, 6.61; N, 3.22.
Sources & evidence
- ORD record
- ord-70981dd25eae4f159d0e4e4bd3bb1222
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124323
Reaction notes
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