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 1840299Notes

Reaction equation

HRID 1840299 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-2f0d0ab6333548c3af9eebd81fb90316
Source dataset
uspto-grants-2004_01
Patent number
US06680319B2

Reaction notes

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