Piperidine → 5-(3-Phenyl-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-2-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 890160Notes

Reaction equation

HRID 890160 reaction equation
[C:1]([O:7][CH2:8][CH2:9][C:10]#[N:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=C[CH:20]=1)C=O.[NH:21]1CCC[CH2:23][CH2:22]1.[C:27]([O:31][CH2:32][CH:33]=[CH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:30])[C:28]#[CH:29].C([O-])(=O)C.[NH4+]>C1C=CC=CC=1.C(O)(=O)C.O>[Cl:12][C:13]1[CH:20]=[C:5]([CH:3]2[C:28]([C:27]([O:31][CH:32]=[CH:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:30])=[CH:29][NH:21][C:22]([CH3:23])=[C:2]2[C:1]([O:7][CH2:8][CH2:9][C:10]#[N:11])=[O:6])[CH:18]=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 517165Ammonium AcetateHCID 123604062-Cyanoethyl 3-oxobutanoateHCID 53746771(3-Phenyl-2-propene-1-yl) propiolate

Product 1

HCID 695901655-(3-Phenyl-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-2-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

466 mg (3.0 mmol) of (2-cyanoethyl) acetoacetate, 0.34 ml (3.0 mmol) of 3-chlorobenzaldehyde and 0.0297 ml of piperidine were heated under reflux in 3.0 ml of benzene for 7 hours while water was removed. The reaction liquid was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was heated to 70° C together with 559 mg (3.0 mmol) of (3-phenyl-2-propene-1-yl) propiolate and 232 mg (3.0 mmol) of ammonium acetate under stirring in 3 ml of acetic acid for 13 hours, then at 120° C. under stirring for 4 hours. Acetic acid was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound.

Workup

  1. customwas removed
  2. customThe reaction liquid
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customAcetic acid was evaporated under reduced pressure
  7. customthe residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-013b148a9ba64dbb8a3e1b2e94f5fe00
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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