Piperidine → Ethyl 2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate

HRID 1164820Notes

Reaction equation

HRID 1164820 reaction equation
[NH2:1][C:2]([CH3:9])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].N1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)C>[CH3:9][C:2]1[NH:1][CH:11]=[CH:12][CH:13]([C:14]2[CH:15]=[CH:4][CH:3]=[CH:2][CH:9]=2)[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 953082-Butenoic acid, 3-amino-, ethyl ester

Product 1

HCID 14652661Ethyl 2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-3-Phenyl-2-propanol (13.8 ml, 0.11 mol) and ethyl 3-amino-2-butenoate (12.9 g, 0.1 mol) were dissolved in 150 ml of absolute ethanol containing 0.5 ml of piperidine. The mixture was heated under reflux for 18 hours followed by removal of the solvent under vacuum to yield 17.6 g of ethyl 1,4-dihydro-2-methyl-4-phenyl-3-pyridinecarboxylate as a brown viscous oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customfollowed by removal of the solvent under vacuum

Sources & evidence

ORD record
ord-bfe328cfc05c47738fca8e7e1b25fa9f
Source dataset
uspto-grants-1990_03
Patent number
US04906624

Reaction notes

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