Triphenylphosphine → [2-(2-Fluoro-1-fluoromethyl-ethoxy)-5-nitro-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

HRID 1820711

Reaction equation

HRID 1820711 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)=[O:12].[F:29][CH2:30][CH:31](O)[CH2:32][F:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[F:29][CH2:30][CH:31]([CH2:32][F:33])[O:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)=[O:12]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 679851,3-Difluoro-2-propanolHCID 5363146Diisopropyl azodicarboxylateHCID 69036826(2-Hydroxy-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Product 1

HCID 69038209[2-(2-Fluoro-1-fluoromethyl-ethoxy)-5-nitro-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanoneYield 113.6%

Procedure

A solution of (2-hydroxy-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (50 mg), 1,3-difluoro-2-propanol [453-13-4] (27 mg), triphenylphosphine (76 mg) and diisopropylazodicarboxylate (48 mg) was refluxed overnight, concentrated in vacuo and purified by column chromatography (SiO2) to yield the title compound as a colorless solid (68 mg). MS (m/e): 474.1 (M+H+, 100%).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-d89d578c0f4d4a0b9f439977106d1db2
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Linked notes

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