Ethanol → HCID 54537305, compound

HRID 2288222Notes

Reaction equation

HRID 2288222 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[C:15]2[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]=2)[C@H:10]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].C(O)C>[Pd].O>[F:27][C:25]([F:26])([F:28])[C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=1)[C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[CH2:30][C:31]1[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=1)=[O:29]

Participants

6

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 54255352HCID 54255352, compound

Product 1

HCID 54537305HCID 54537305, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(4-fluorobenzyl)piperazine (7.92 g), ammonium formate (2.38 g) and 10% palladium charcoal (0.79 g) in a mixed solvent of ethanol (80 ml) and water (8 ml) was stirred for 1.5 hours at 60° C. under nitrogen atmosphere. The reaction mixture was cooled to room temperature and filtered through Celite® pad. The filtrate was concentrated under reduced pressure and the residue was dissolved into ethyl acetate. The solution was washed with water and brine successively, dried over magnesium sulfate, and evaporated under reduced pressure to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(4-fluorobenzyl)piperazine (6.04 g) as an oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite® pad
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved into ethyl acetate
  5. washThe solution was washed with water and brine successively
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ad9bd4562689429f8cee958b3edd7371
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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