1-Benzyl-4-(cyclopropylcarbonyl)piperazine → 1-(Cyclopropylcarbonyl)piperazine

HRID 1972725Notes

Reaction equation

HRID 1972725 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].CCO>[CH:16]1([C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:15])[CH2:17][CH2:18]1

Participants

4

Reactant 1

HCID 12200501-Benzyl-4-(cyclopropylcarbonyl)piperazine

Product 1

HCID 20642351-(Cyclopropylcarbonyl)piperazineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

10% Palladium on carbon (175 mg, 10% by wt.) was placed under an inert atmosphere and suspended in EtOH (5 mL). A solution of (4-benzyl-piperazin-1-yl)-cyclopropyl-methanone (1.75 g, 7.16 mmol) dissolved in EtOH (25 mL) was added. The reaction mixture was placed under H2 atmosphere (1 atmosphere pressure) and stirred overnight. The resulting mixture was filtered through a pad of Celite® and the solvent was concentrated in vacuo to give 1.07 g (97%) of the title compound as a clear oil. 1H-NMR (300 MHz, CD3OD) 3.74 (broad s, 2H), 3.57 (broad s, 2H), 2.87 (broad s, 2H), 2.80 (broad s, 2H), 1.97 to 1.91 (m, 1H), 0.89 to 0.78 (m, 4H); ES-MS m/z 154.9 [M+H]+, RT (min) 1.02.

Workup

  1. additionwas added
  2. filtrationThe resulting mixture was filtered through a pad of Celite®
  3. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-ba99f7e8a90a4003a7048ff6a6fc849b
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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