Felbinac → 1-(2-Biphenyl-4-yl-ethyl)-3-(4-trifluoromethyl-phenoxymethyl)-piperidine

HRID 720055Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][C:17]3C4C(=CC=CC=4)N[CH:18]=3)[CH2:10]2)=[CH:5][CH:4]=1.[C:30]1([C:40]2[CH:45]=CC=[CH:42][CH:41]=2)[CH:35]=[CH:34][C:33](CC(O)=O)=[CH:32][CH:31]=1>>[C:40]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:45]=[CH:18][C:17]([CH2:16][CH2:15][N:11]2[CH2:12][CH2:13][CH2:14][CH:9]([CH2:8][O:7][C:6]3[CH:26]=[CH:27][C:3]([C:2]([F:1])([F:28])[F:29])=[CH:4][CH:5]=3)[CH2:10]2)=[CH:42][CH:41]=1

Participants

Reactant 2

HCID 3332Felbinac

HCID 219019863-{2-[3-(4-Trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-ethyl}-1H-indole

Product 1

HCID 219019491-(2-Biphenyl-4-yl-ethyl)-3-(4-trifluoromethyl-phenoxymethyl)-piperidine

Procedure

Following exactly the same two step procedure used in the previous example for the preparation of 3-{2-[3-(4-Trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-ethyl}-1H-indole but using biphenyl-4-yl-acetic acid in place of (1H-Indol-3-yl)-acetic acid, 1-(2-Biphenyl-4-yl-ethyl)-3-(4-trifluoromethyl-phenoxymethyl)-piperidine was obtained in 54% overall yield from 0.19 mmol of 3-(4-Trifluoromethyl-phenoxymethyl)-piperidine, 181. Data for this compound: MS 440 (M++1).

Sources & evidence

ORD record: ord-ce8cad224fc7435583e2c8fbfa6586d6
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132551B2

Reaction notes

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