Water → 1-(4-{[2-(3-Trifluoromethyl-phenyl)-ethylamino]-methyl}-phenyl)-cyclopropanecarbonitrile

HRID 855187Notes

Reaction equation

HRID 855187 reaction equation
[BH4-].[Na+].[C:3]([C:5]1([C:8]2[CH:33]=[CH:32][C:11]([CH2:12][N:13]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)C(=O)C(F)(F)F)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)#[N:4].O>C(O)C>[F:29][C:28]([F:30])([F:31])[C:24]1[CH:23]=[C:22]([CH2:21][CH2:20][NH:13][CH2:12][C:11]2[CH:10]=[CH:9][C:8]([C:5]3([C:3]#[N:4])[CH2:6][CH2:7]3)=[CH:33][CH:32]=2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86603033N-[4-(1-cyano-cyclopropyl)-benzyl]-2,2,2-trifluoro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-acetamide

Product 1

HCID 693424741-(4-{[2-(3-Trifluoromethyl-phenyl)-ethylamino]-methyl}-phenyl)-cyclopropanecarbonitrileYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

46 mg (1.23 mmol) of sodium borohydride were added to 135 mg (0.31 mg) of N-[4-(1-cyano-cyclopropyl)-benzyl]-2,2,2-trifluoro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-acetamide dissolved in 3.1 ml ethanol under nitrogen. The reaction mixture was stirred at rt for 3 h. Under ice bath cooling water was added and the reaction mixture was extracted twice with EtOAc. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (25 g silica gel; methylene chloride/methanol=19:1) to yield 81 mg (77%) of 1-(4-{[2-(3-trifluoromethyl-phenyl)-ethylamino]-methyl}-phenyl)-cyclopropanecarbonitrile as a colorless oil. 1HNMR (DMSO-d6, 300 MHz): δ 7.61-7.47 (m, 4H), 7.30 (d, 2H), 7.24 (d, 2H), 3.69 (s, 2H), 2.81 (t, 2H), 2.73 (t, 2H), 1.72 (m, 2H), 1.44 (m, 2H).

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted twice with EtOAc
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography (25 g silica gel; methylene chloride/methanol=19:1)

Sources & evidence

ORD record
ord-dce975a93f264513b577b2cb81595cb7
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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