Chloroacetone → HCID 11558165, compound

HRID 856015Notes

Reaction equation

HRID 856015 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)C(C)C)C.Cl[CH2:17][C:18](=[O:20])[CH3:19].[N:21]1([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(#N)C>[O:20]=[C:18]([CH3:19])[CH2:17][N:24]1[CH2:23][CH2:22][N:21]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 11558165HCID 11558165, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (1.27 g, 9.22 mmol), N-ethyldiisopropylamine (0.80 ml, 4.61 mmol), and chloroacetone (1.22 ml, 13.83 mmol) were added to a solution of benzyl piperazine-1-carboxylate (2.03 g, 90.22 mmol) in acetonitrile(20 ml), and the mixture was heated under reflux for 2 hours. The insoluble substances were removed by filtration and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography(methylene chloride/methanol=100/1) to afford benzyl 4-(2-oxopropyl)piperazine-1-carboxylate (2.24 g, yield 88%) as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe insoluble substances were removed by filtration
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography(methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-3fae510a45ed4a9f9af3666d7a866882
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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