Tert-butyl 4-(cyclopropanecarbonyl)piperazine-1-carboxylate → 1-(Cyclopropylcarbonyl)piperazine Hydrochloride

HRID 1467540Notes

Reaction equation

HRID 1467540 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[ClH:19].CO>CO>[ClH:19].[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 968936Tert-butyl 4-(cyclopropanecarbonyl)piperazine-1-carboxylateHCID 21893726Hydrochloride methanol

Product 1

HCID 208479551-(Cyclopropylcarbonyl)piperazine HydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of compound tert-butyl 4-(cyclopropanecarbonyl)piperazine-1-carboxylate (3.7 g, 14.5 mmol) in methanol (15 mL) was added hydrochloride/methanol (15 mL, 3M)) at 0° C. After the addition, the mixture was allowed to stir at room temperature overnight. The mixture was concentrated to give cyclopropyl(piperazin-1-yl)methanone hydrochloride (2.74 g, yield 100%) as an off-white solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.71-0.76 (m, 4H), 1.96-2.03 (m, 1H), 3.04-3.16 (m, 4H), 3.69-4.08 (m, 4H), 9.58 (s, 2H); LC-MS (ESI) m/z: 155 (M+1)+.

Workup

  1. additionAfter the addition
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-3166ed02569d4405ae61dbcc13e06022
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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