Ammonium formate → 1-[2-(Trifluoromethyl)benzoyl]piperazine

HRID 1177865Notes

Reaction equation

HRID 1177865 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:29])([F:28])[F:27])=[O:19])[CH2:14][CH2:13]1)C1C=CC=CC=1>CO.[Pd]>[N:15]1([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:28])([F:27])[F:29])=[O:19])[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 17683255HCID 17683255, compound

Product 1

HCID 167337841-[2-(Trifluoromethyl)benzoyl]piperazineYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

Ammonium formate (15.5 g, 247.126 mmol) was added to (4-benzyl-piperazin-1-yl)-(2-trifluoromethyl-phenyl)-methanone (8.6 g, 24.71 mmol) in MeOH (40 mL). Pd/C (1.8 g in 2 mL water) was then added and the resulting mixture was heated to reflux at 75° C. for 4 hours. The reaction mixture was then filtered through a bed of celite bed and the methanol was removed. EtOAc and water were then added to the residue and the organic layer was extracted, washed with 10% NaOH solution, brine, dried over sodium sulphate, and concentrated to afford 5.5 g (86% yield) of piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone.

Workup

  1. temperaturethe resulting mixture was heated
  2. filtrationThe reaction mixture was then filtered through a bed of celite bed
  3. customthe methanol was removed
  4. additionEtOAc and water were then added to the residue
  5. extractionthe organic layer was extracted
  6. washwashed with 10% NaOH solution, brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c5817061e77c4a6e986d1beecb13ebb9
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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