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

HRID 730890Notes

Reaction equation

HRID 730890 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-1b8325a8c6d5448ba5685f780a924e28
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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