HCID 17683255, compound → 1-[2-(Trifluoromethyl)benzoyl]piperazine

HRID 1665587Notes

Reaction equation

HRID 1665587 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1>O.CO.[Pd]>[N:11]1([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:24])([F:23])[F:25])=[O:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 1

HCID 17683255HCID 17683255, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

NH4COOH (15.5 g, 247 mmol) and 10% Pd/C (1.8 g) in water (2 mL) were added to a stirred solution of (4-benzyl-piperazin-1-yl)-(2-trifluoromethyl-phenyl)-methanone (8.6 g, 24.7 mmol) in MeOH (40 mL) and the resulting mixture was heated to reflux at 75° C. for 4 hrs. The reaction mixture was then filtered over celite and the filtrate evaporated. The resulting residue was dissolved in ethyl acetate, washed with 10% NaOH solution then brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford 5.5 g (86%) of piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone. 1H NMR: (DMSO-d6): δ 7.8 (d, 1H), 7.7 (t, 1H), 7.6 (t, 1H), 7.4 (d, 1H), 3.5 (m, 2H), 3.0 (m, 2H), 2.7 (m, 5H).

Workup

  1. temperaturethe resulting mixture was heated
  2. filtrationThe reaction mixture was then filtered over celite
  3. customthe filtrate evaporated
  4. dissolutionThe resulting residue was dissolved in ethyl acetate
  5. washwashed with 10% NaOH solution
  6. dry with materialbrine solution, dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25683c178b354bc98ffc34429179486d
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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