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

HRID 881305Notes

Reaction equation

HRID 881305 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 hours the reaction mixture was cooled, filtered through celite, diluted with chloroform, washed with brine, dried (MgSO4) and the solvent 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 N-methyl-2-piperazin-1-yl-isobutyramide, which was isolated as the hydrochloride salt.

Workup

  1. temperatureat reflux
  2. temperatureAfter 24 hours 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 removed in vacuo

Sources & evidence

ORD record
ord-e9546a2b72a14461b6e2c6558594fc1e
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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