Ethyl Acrylate → Ethyl 3-[4,4']bipiperidinyl-1-yl-propionate

HRID 730636Notes

Reaction equation

HRID 730636 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].[N:8]1(C(OC(C)(C)C)=O)[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1>CCO>[N:8]1([CH2:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 8821Ethyl Acrylate2×HCID 117475994,4'-Bipiperidine, 1-boc protected

Product 1

HCID 57807790Ethyl 3-[4,4']bipiperidinyl-1-yl-propionate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.4 mL (40.6 mmol) ethyl acrylate were added to a solution of 10.0 g (37.3 mmol) tert. butyl [4,4′]bipiperidinyl-1-carboxylate in 100 mL EtOH and the reaction mixture was refluxed for 2 h. To complete the reaction a further 1 mL (9.2 mmol) ethyl acrylate were added, the mixture was refluxed for 1 h and left overnight at RT. The solvent was eliminated i. vac. and the crude product was further reacted without any purification.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. additionwere added
  3. temperaturethe mixture was refluxed for 1 h

Sources & evidence

ORD record
ord-1c53c695232e43aa9fc1d37cb203bd87
Source dataset
uspto-grants-2009_09
Patent number
US07582625B2

Reaction notes

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