Potassium Carbonate → 1,1-Dimethylethyl 4-(4-morpholinylcarbonyl)-1-piperazinecarboxylate

HRID 502519Notes

Reaction equation

HRID 502519 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:14](=[O:17])([O-])[O-].[K+].[K+]>C(#N)C.ClCCl>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:1]([N:8]2[CH2:13][CH2:14][O:17][CH2:10][CH2:9]2)=[O:2])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 100176291,1-Dimethylethyl 4-(4-morpholinylcarbonyl)-1-piperazinecarboxylateYield 195%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Amine preparation: A mixture of 4-morpholinocarbonyl chloride (0.38 ml), 1-BOC-piperazine (552 mg) and potassium carbonate (439 mg) in acetonitrile (7 mL) was stirred at room temperature for 3 hours. The reaction mixture was then diluted with dichloromethane, washed with brine, dried (MgSO4) and the solvent removed in vacuo to yield 4-(morpholine-4-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester (865 mg). Treatment of this compound with HCl in dichloromethane/methanol yielded the title compound, which was isolated as the hydrochloride salt.

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a32381d049874e97a8625957bfc9a6a3
Source dataset
uspto-grants-2010_08
Patent number
US07776856B2

Reaction notes

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