Potassium Carbonate → Tert-butyl 4-(cyclopropanecarbonyl)piperazine-1-carboxylate

HRID 1992447Notes

Reaction equation

HRID 1992447 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH:1]1([C:4]([N:17]2[CH2:16][CH2:15][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:19][CH2:18]2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77637Cyclopropanecarbonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 968936Tert-butyl 4-(cyclopropanecarbonyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopropanoyl 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 to give the title compound (210 mg) as an oil.

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

Sources & evidence

ORD record
ord-7c10d017fdf64a6a9b37a3509fa8cbf8
Source dataset
uspto-grants-2010_01
Patent number
US07648990B2

Reaction notes

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