4-Benzyl-N-methylpiperazine-1-carboxamide → N-methylpiperazine-1-carboxamide

HRID 1972719Notes

Reaction equation

HRID 1972719 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[CH2:10][CH2:9][N:8](CC2C=CC=CC=2)[CH2:7][CH2:6]1)=[O:4]>[Pd].CCO.CCO.C1COCC1>[CH3:1][NH:2][C:3]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 1

HCID 166458044-Benzyl-N-methylpiperazine-1-carboxamide

Product 1

HCID 11672770N-methylpiperazine-1-carboxamideYield 99.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Palladium on carbon (300 mg, 10% by wt.) was placed under an inert atmosphere and suspended in EtOH (10 mL). A solution of 4-benzyl-piperazine-1-carboxylic acid methylamide (1.50 g, 6.43 mmol) dissolved in 2:1 v/v EtOH/THF (96 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 916 mg (99%) of the title compound as clear oil. 1H-NMR (300 MHz, DMSO-d6) 6.30 (broad d, 1H), 3.15 to 3.12 (m, 5H), 2.59 to 2.55 (m, 4H), 2.53 (d, 3H).

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-75541de7266c47e0b84cfe446fb658a1
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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