Potassium Carbonate → HCID 11558165, compound

HRID 1668688Notes

Reaction equation

HRID 1668688 reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.ClC[CH2:19][C:20](=[O:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)C>[C:20]([CH2:21][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2][CH2:3]1)(=[O:22])[CH3:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 806084-Chloro-2-butanoneHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 11558165HCID 11558165, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of benzyl 1-piperazinecarboxylate (4.1 ml), chloromethyl acetone (1.8 ml) and potassium carbonate (8.8 g) in acetonitrile (40 ml) was stirred overnight at ambient temperature. The reaction mixture was diluted in diethyl ether and the solution was partitioned between diethyl ether and water. The water phase was extracted with diethyl ether, the organic phases were combined and washed with water, brine, dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography using dichloromethane/methanol saturated with ammonia (3.5 M) (98/2). Evaporation of the solvent gave benzyl 4-(acetylmethyl)-1-piperazinecarboxylate (3.7 g, 63%) as a yellow oil.

Workup

  1. customthe solution was partitioned between diethyl ether and water
  2. extractionThe water phase was extracted with diethyl ether
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by flash chromatography
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-510105aaf4104320a1962a4dd5e41bd3
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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