Dimethylcarbamoyl Chloride → tert-Butyl 4-(dimethylcarbamoyl)piperazine-1-carboxylate

HRID 421629Notes

Reaction equation

HRID 421629 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(N(CC)CC)C.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>O1CCCC1.ClCCl>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:23](=[O:24])[N:22]([CH3:26])[CH3:21])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22665738tert-Butyl 4-(dimethylcarbamoyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Amine preparation: to a solution of 1-BOC-piperazine (867 mg) in dry tetrahydrofuran (8 mL) was added triethylamine (0.97 mL) followed by dimethylcarbamoyl chloride (0.51 mL). After stirring for 24 hours the reaction mixture was then diluted with dichloromethane, washed with brine, dried (MgSO4) and the solvent was removed in vacuo to yield 4-dimethylcarbamoyl-piperazine-1-carboxylic acid tert-butyl ester (940 mg). Treatment of this compound with HCl in dichloromethane/methanol yielded the compound 113.

Workup

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

Sources & evidence

ORD record
ord-29dc18056d914a928cbba1fe069ed171
Source dataset
uspto-grants-2012_01
Patent number
US08101607B2

Reaction notes

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