Potassium Carbonate → HCID 57420344, compound

HRID 2365178Notes

Reaction equation

HRID 2365178 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[C:5](Br)([CH3:7])[CH3:6])[CH3:2].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:9])([CH3:7])[CH3:6])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

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 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a stirring solution of ethyl-2-bromoisobutyrate (2.65 g, 13.6 mmol) in anhydrous acetonitrile (25 mL) at room temperature was added tert-butyl-1-piperazinecarboxylate (2.48 g, 13.3 mmol) followed by potassium carbonate (1.88 g, 13.6 mmol). The mixture was heated to 85° C. overnight. The cooled reaction mixture was partitioned between ethyl acetate and water. The combined organic layers were washed with brine, separated and dried (MgSO4). The crude product was purified by column chromatography to yield 4-(1-ethoxycarbonyl-1-methyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester as a colourless oil (1.28 g).

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. washThe combined organic layers were washed with brine
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-d605df63fba34b7198f51476a250abc1
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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