Potassium Carbonate → HCID 57420344, compound

HRID 2365181Notes

Reaction equation

HRID 2365181 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:22])[CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 57420344HCID 57420344, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl-1-piperazinecarboxylate (1.20 g) in acetonitrile (15 mL) was added ethyl 2-bromoisobutyrate (5.00 g) followed by potassium carbonate (0.975 g). The reaction mixture was heated at 80° C. for 12 hours, then cooled and partitioned between water and dichloromethane. The organic layer was washed with brine, dried (MgSO4). The solvent was evaporated and the residue purified by flash chromatography to give 4-(1-ethoxycarbonyl-1-methyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (2.19 g).

Workup

  1. temperaturecooled
  2. custompartitioned between water and dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-5b37a25122714e52b543a6ae9cfcba4c
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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