Acetic Acid → HCID 57849499, compound

HRID 737114Notes

Reaction equation

HRID 737114 reaction equation
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])=[CH:16][CH:15]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[BH-](O[C:40](=O)[CH3:41])OC(=O)C)(=O)C.[Na+].[C:44](O)(=O)C>ClC(Cl)C.CC(C)=O.ClCCl>[CH:40]([N:12]1[CH2:11][CH2:10][N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:28])([F:29])[F:27])=[CH:16][CH:15]=2)[CH2:8][CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:41])[CH3:44]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 57849459HCID 57849459, compound

Product 1

HCID 57849499HCID 57849499, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

100 mg of 3-phenyl-1-(2′-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine was dissolved in a 2:1 mixture of dichloroethane and acetone, 2 equiv. of sodium triacetoxyborohydride was added followed by 30 μL of acetic acid. The reaction was stirred at room temperature under nitrogen overnight. The reaction was diluted with 5 mL of dichloromethane. The reaction mixture was washed with 1M aqueous sodium hydroxide solution and brine, then dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by column chromatography to afford the title compound. Yield 41% ES MS m/z 439.

Workup

  1. additionwas added
  2. washThe reaction mixture was washed with 1M aqueous sodium hydroxide solution and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-ce04fb94b13342cfb67934d4b6d03f6d
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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