tert-Butyl piperazine-1-carboxylate → 4-(1-Methyl-1-methylcarbamoyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1689882Notes

Reaction equation

HRID 1689882 reaction equation
Br[C:2]([CH3:8])([CH3:7])[C:3]([NH:5][CH3:6])=[O:4].[C:9]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>C1(C)C=CC=CC=1.[Ag]=O>[C:12]([O:11][C:9]([N:16]1[CH2:21][CH2:20][N:19]([C:2]([CH3:8])([C:3](=[O:4])[NH:5][CH3:6])[CH3:7])[CH2:18][CH2:17]1)=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 2875602-Bromo-N,2-dimethylpropanamide

Product 1

HCID 574939964-(1-Methyl-1-methylcarbamoyl-ethyl)-piperazine-1-carboxylic acid tert-butyl esterYield 93.2%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-2,N-dimethyl-propionamide (312 mg), 1-BOC-piperazine (323 mg) and silver oxide (800 mg) was stirred in toluene (5 mL) at reflux. After 24 h the reaction mixture was cooled, filtered through celite, diluted with chloroform, washed with brine, dried (MgSO4) and the solvent was removed in vacuo to yield 4-(1-methyl-1-methylcarbamoyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (461 mg). Removal of the BOC group with HCl yielded the desired compound, which was isolated as the hydrochloride salt.

Workup

  1. temperatureat reflux
  2. temperatureAfter 24 h the reaction mixture was cooled
  3. filtrationfiltered through celite
  4. additiondiluted with chloroform
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ec0760674a704702a3d1ff9cec548e1e
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

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