3-{4-[2-(2,2,2-Trifluoroethoxy)phenyl]piperazin-1-yl}propylamine → 3-Phenyl-N-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]propyl]isoxazole-4-carboxamide

HRID 840126Notes

Reaction equation

HRID 840126 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([OH:15])=O)=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][C:34]([F:37])([F:36])[F:35])[CH2:22][CH2:21]1.NCCCN1CCN(C2C=CC(F)=CC=2OCC(F)(F)F)CC1>>[C:5]1([C:8]2[C:12]([C:13]([NH:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][N:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH2:33][C:34]([F:36])([F:37])[F:35])[CH2:24][CH2:25]3)=[O:15])=[CH:11][O:10][N:9]=2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 105674903-{4-[2-(2,2,2-Trifluoroethoxy)phenyl]piperazin-1-yl}propylamineHCID 234478853-(4-Fluoro-phenyl)-isoxazole-4-carboxylic acidHCID 234479111-(3-Aminopropyl)-4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazine

Product 1

HCID 234479053-Phenyl-N-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]propyl]isoxazole-4-carboxamideYield 88%

Procedure

The title compound was prepared according to the procedure described in Example 8, but substituting compound 15B for Compound 8D and Compound 12B for Compound 8B. Purification by flash chromatography (ethyl acetate-2 N ammonia in methanol 95:5) yielded the title product (88%). M.p. 94.5-95.6° C.

Workup

  1. customThe title compound was prepared
  2. customPurification by flash chromatography (ethyl acetate-2 N ammonia in methanol 95:5)

Sources & evidence

ORD record
ord-850b8ee885204d4f80841c889eb9ca48
Source dataset
uspto-grants-2002_04
Patent number
US06365591B1

Reaction notes

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