Chloroacetone → tert-Butyl 4-isobutyrylpiperazine-1-carboxylate

HRID 1992448Notes

Reaction equation

HRID 1992448 reaction equation
[C:1](=O)([CH3:4])[CH2:2]Cl.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[C:19](=[O:22])([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH3:2][CH:1]([CH3:4])[C:19]([N:16]1[CH2:17][CH2:18][N:13]([C:11]([O:10][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:12])[CH2:14][CH2:15]1)=[O:22]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 60708297tert-Butyl 4-isobutyrylpiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isopropanoyl chloride (112 μL) was added to a mixture of N-tert-butoxycarbonylpiperazine (200 mg) and an excess of potassium carbonate in anhydrous DCM (10 mL) under a nitrogen atmosphere. The mixture was stirred at r.t. for 18 hours, then it was filtered off from inorganics. The organic phase was diluted with Et2O (20 mL) and washed with 1N hydrochloric acid solution (10 mL). The aqueous phase was made basic with 1N sodium hydroxide solution and extracted twice with DCM. The combined organic layers were dried and concentrated in vacuo and the residue was purified by flash chromatography (AcOEt 100%) to give the title compound (133 mg) as a white solid.

Workup

  1. filtrationit was filtered off from inorganics
  2. additionThe organic phase was diluted with Et2O (20 mL)
  3. washwashed with 1N hydrochloric acid solution (10 mL)
  4. extractionextracted twice with DCM
  5. customThe combined organic layers were dried
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by flash chromatography (AcOEt 100%)

Sources & evidence

ORD record
ord-611211fd9f47428cb9f48a19cd925fbc
Source dataset
uspto-grants-2010_01
Patent number
US07648990B2

Reaction notes

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