Acetic Acid → HCID 57849588, compound

HRID 737121Notes

Reaction equation

HRID 737121 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]=[C:24]([CH3:26])[CH:23]=[CH:22][C:21]=4[Cl: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:38](=O)[CH3:39])OC(=O)C)(=O)C.[Na+].[C:42](O)(=O)C>ClC(Cl)C.CC(C)=O.ClCCl>[CH:38]([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]=[C:24]([CH3:26])[CH:23]=[CH:22][C:21]=3[Cl: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)([CH3:39])[CH3:42]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 57849464HCID 57849464, compound

Product 1

HCID 57849588HCID 57849588, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

This compound could be made the following manner: 100 mg of 3-phenyl-1-(2′-chloro-5′-methyl-biphenyl-4-ylmethyl)-piperazine would be dissolved in a 2:1 mixture of dichloroethane and acetone, 2 equiv. of sodium triacetoxyborohydride would be added followed by 30 μL of acetic acid. The reaction would be stirred at room temperature under nitrogen overnight. The reaction would be diluted with 5 mL of dichloromethane. The reaction mixture would be washed with 1M aqueous sodium hydroxide solution and brine, then dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue would be purified by column chromatography to afford the title compound.

Workup

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

Sources & evidence

ORD record
ord-e29bd7605b5343aba4237fa8881c023f
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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