Benzyl 4-(Isopropylcarbamoyl)piperazine-1-carboxylate → N-Isopropylpiperazine-1-carboxamide

HRID 922405Notes

Reaction equation

HRID 922405 reaction equation
[CH:1]([NH:4][C:5]([N:7]1[CH2:12][CH2:11][N:10](C(OCC2C=CC=CC=2)=O)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[CH:1]([NH:4][C:5]([N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 86719361Benzyl 4-(Isopropylcarbamoyl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 16740267N-Isopropylpiperazine-1-carboxamideYield 130.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 4-(isopropylcarbamoyl)piperazine-1-carboxylate (3, 3.94 g, 12.9 mmol) in methanol (100 mL) was added 10% Pd/C (50% wet, 0.400 g) and the mixture was stirred under 1 atmosphere of hydrogen for 16 h. After this time, the mixture was filtered through Celite and the filtrate concentrated to afford the title compound (2.88 g, >99%): 1H NMR (300 MHz, CD3OD) δ 4.00-3.80 (m, 1H), 3.45-3.35 (m, 4H), 2.88-2.78 (m, 4H), 1.13 (d, J=6.5 Hz, 6H); Multimode MS m/z 172 [M+H]+.

Workup

  1. filtrationAfter this time, the mixture was filtered through Celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f64017b7a1b545a3a8b4402028b3b5a5
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Reaction notes

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