Potassium Carbonate → Ethyl α,α-dimethyl-4-[(phenylmethoxy)carbonyl]-1-piperazineacetate

HRID 1796973Notes

Reaction equation

HRID 1796973 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:25])[C:21](Br)([CH3:23])[CH3:22])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:21]([C:20]([O:19][CH2:17][CH3:18])=[O:25])([CH3:23])[CH3:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 69583640Ethyl α,α-dimethyl-4-[(phenylmethoxy)carbonyl]-1-piperazineacetateYield 77%

Conditions

Temperature
150 °C

Procedure

A mixture of piperazine-1-carboxylic acid benzyl ester (8.8 g, 40 mmol), 2-bromo-2-methylpropionic acid ethyl ester and potassium carbonate was stirred at 150° C. for 24 h. On cooling, the resulting mixture was partitioned between dichloromethane and water. The organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure to give 4-(1-Ethoxycarbonyl-1-methyl-ethyl)-piperazine-1-carboxylic acid benzyl ester (10.2 g, 77%) as an oil.

Workup

  1. temperatureOn cooling
  2. customthe resulting mixture was partitioned between dichloromethane and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9dbc9bdc700441fc997a3d67b43e23b3
Source dataset
uspto-grants-2006_04
Patent number
US07034016B2

Reaction notes

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