Water → HCID 21308240, compound

HRID 1418567Notes

Reaction equation

HRID 1418567 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][NH:12][CH2:11][CH2:10][N:9]1[C:14](=[O:29])[C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[O:36]([CH2:43][C:44](Cl)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.O>CN(C)C=O>[CH2:1]([C@@H:8]1[CH2:13][N:12]([C:44](=[O:45])[CH2:43][O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:11][CH2:10][N:9]1[C:14](=[O:29])[C:15]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049Pyridine2×HCID 69703Phenoxyacetyl chloride2×HCID 54243495HCID 54243495, compound

Product 1

HCID 21308240HCID 21308240, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred solution of (2R)-2-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]piperazine (0.3 g) in dry dimethylformamide (3 ml) containing dry pyridine (0.06 ml) was added a solution of 2-phenoxyacetyl chloride (0.12 g) in dry dimethylformamide (1 ml) at 0° C., and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 30 minutes. Additional pyridine (0.02 ml) and a solution of 2-phenoxyacetyl chloride (0.025 g) in dry dimethylformamide (0.3 ml) were added to the reaction mixture. After being stirred for 30 minutes, the mixture was poured into water (43 ml) and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by a silica gel column chromatography. Elution with toluene-ethyl acetate afforded (2R)-2-benzyl-l-[3,5-bis(trifluoromethyl)benzoyl]-4-(2-phenoxyacetyl)piperazine (0.34 g) as a white powder.

Workup

  1. waitat room temperature for 30 minutes
  2. stirringAfter being stirred for 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by a silica gel column chromatography
  8. washElution with toluene-ethyl acetate

Sources & evidence

ORD record
ord-d0a20190d06442298dff880804442177
Source dataset
uspto-grants-1999_03
Patent number
US05883098

Reaction notes

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