Potassium Carbonate → 1-[2-(4-Hydroxy-3-fluorophenoxy)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[F: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[F:34]Participants
4
Procedure
The title compound was prepared from 4-(4-fluorobenzyl)piperidine hydrochloride (344 mg, 1.50 mmol), 2-(4-benzoxy-3-fluorophenoxy)ethyl bromide (487 mg, 1.50 mmol), potassium carbonate (518 mg, 3.75 mmol) in two steps as white-off solid (277 mg), mp 184-186° C. 1H NMR (CD3OD) 1.40 (m, 2 H), 1.709 (m, 3 H), 2.424 (d, J=4.8 Hz, 2 H), 2.850 (m, 2 H), 3.319 (m, 2 H), 3.443 (d, J=12.0 Hz, 2 H), 4.087 (s, 2 H), 6.50 (m, 1 H), 6.642 (m, 2 H), 6.833 (m, 2 H), 7.021 (m, 2 H).
Sources & evidence
- ORD record
- ord-9ff23e1aed6f4de8906ea56444e5a6a6
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124323
Reaction notes
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