2-Methylcarbamoyl-piperazine-1,4-dicarboxylic acid dibenzyl ester → N-Methylpiperazine-2-carboxamide

HRID 912949Notes

Reaction equation

HRID 912949 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14](C(OCC2C=CC=CC=2)=O)[CH2:13][CH:12]1[C:27](=[O:30])[NH:28][CH3:29])=O)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:29][NH:28][C:27]([CH:12]1[CH2:13][NH:14][CH2:15][CH2:16][NH:11]1)=[O:30]

Participants

4

Reactant 1

HCID 674009652-Methylcarbamoyl-piperazine-1,4-dicarboxylic acid dibenzyl ester

Product 1

HCID 14722545N-Methylpiperazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-methylcarbamoyl-piperazine-1,4-dicarboxylic acid dibenzyl ester from step (b) above (1.64 g, 4.0 mmol) and 10% Pd/C (42 mg, 0.04 mmol, Aldrich) in ethanol (10 mL) was vigorously stirred under hydrogen atmosphere for 4 h at room temperature. The catalyst was filtered through Celite® pad and the filter cake was washed with EtOH. The filtrate was evaporated in vacuo to give the title compound, which was used in the next step without additional purification. MS (ESI, pos. ion) m/e: 144 (M+1).

Workup

  1. filtrationThe catalyst was filtered through Celite® pad
  2. washthe filter cake was washed with EtOH
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-15fae098254d4b699d2bdeba13d8ed2c
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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