Hydrochloride methanol → 2-Methyl-1-(piperazin-1-yl)propan-1-one

HRID 907809Notes

Reaction equation

HRID 907809 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].Cl.CO>CO>[CH3:3][CH:2]([CH3:4])[C:1]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 60708297tert-Butyl 4-isobutyrylpiperazine-1-carboxylate

Product 1

HCID 27614092-Methyl-1-(piperazin-1-yl)propan-1-oneYield 132.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of tert-butyl 4-isobutyrylpiperazine-1-carboxylate (6.8 g, 26.5 mmol) in methanol (15 mL) was added hydrochloride/methanol (30 mL, 3M)) at 0° C. After the addition, the mixture was allowed to stir at room temperature overnight. The mixture was concentrated to give 2-methyl-1-(piperazin-1-yl)propan-1-one (5.5 g, yield 100%) as an off-white solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.99-1.00 (d, J=6.4 Hz, 6H), 2.84-2.89 (m, 1H), 3.03-3.07 (d, 4H), 3.68-3.74 (d, 4H), 9.58 (s, 2H); LC-MS (ESI) m/z: 157(M+1)+.

Workup

  1. additionAfter the addition
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-54f7d4db68944c30928748191e45ee14
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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