HCID 21618684, compound → tert-Butyl 2-methylpiperazine-1-carboxylate

HRID 1968064Notes

Reaction equation

HRID 1968064 reaction equation
[CH3:1][CH:2]1[CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[CH2:5][CH2:4][N:3]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CO.[Pd]>[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19]

Participants

4

Reactant 1

HCID 21618684HCID 21618684, compound

Product 1

HCID 15087784tert-Butyl 2-methylpiperazine-1-carboxylateYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-benzyl 1-tert-butyl 2-methylpiperazine-1,4-dicarboxylate (4.8 g, 14.4 mmol) in methanol (25 mL) was added 480 mg of 10% Pd/C and stirred at room temperature under hydrogen overnight. Filtered and concentrated to give the title product (2.8 g, yield 97%) as colorless oil. 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.21 (d, J=6.8 Hz, 3H), 1.46 (s, 9H), 2.64-2.70 (m, 1H), 2.74-2.78 (m, 1H), 2.88-3.01 (m, 3H), 3.78 (d, J=12.4 Hz, 1H), 4.16 (m, 1H); LC-MS (ESI) m/z: 201 (M+1)+.

Workup

  1. filtrationFiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f52b60e78083407aaa8844b3b8be8724
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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