Water → Ethyl 1-(cyclopropylcarbonyl)piperidine-4-carboxylate

HRID 1260964

Reaction equation

HRID 1260964 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH:19]1([C:22](Cl)=[O:23])[CH2:21][CH2:20]1.O>C1COCC1>[CH:19]1([C:22]([N:1]2[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]2)=[O:23])[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 10036613Ethyl 1-(cyclopropylcarbonyl)piperidine-4-carboxylateYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl piperidine-4-carboxylate (5 g) and triethylamine (5.3 mL) in THF (100 mL) was added cyclopropylcarbonyl chloride (3.99 g) at 0° C., and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and brine and dried, and the solvent was evaporated under reduced pressure to give ethyl 1-(cyclopropylcarbonyl)piperidine-4-carboxylate (6.32 g, 81%) as a pale yellow oil.

Workup

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-232ac1c93022448d8e8092d3056a9faf
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Linked notes

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