Piperidine → Ethyl 2-acetoxymethyl-4-(3-chlorophenyl)-6-methyl-5-(3-phenyl-2-propene-1-ylcarbamoyl)-1,4-dihydropyridine-3-carboxylate

HRID 1700341Notes

Reaction equation

HRID 1700341 reaction equation
O=[C:2]([CH3:16])[CH2:3][C:4]([NH:6][CH2:7][CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5].[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O.[NH:26]1CCCCC1.[C:32]([O:35][CH2:36][C:37](=O)[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:34])[CH3:33].C([O-])(=O)C.[NH4+]>C1C=CC=CC=1.CC(O)C.O>[C:32]([O:35][CH2:36][C:37]1[NH:26][C:2]([CH3:16])=[C:3]([C:4](=[O:5])[NH:6][CH2:7][CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:21]([C:20]2[CH:23]=[CH:24][CH:25]=[C:18]([Cl:17])[CH:19]=2)[C:38]=1[C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:34])[CH3:33]

Participants

9

Reactant 5

HCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 517165Ammonium AcetateHCID 11480907Ethyl 4-acetoxyacetoacetateHCID 53935748HCID 53935748, compound

Product 1

HCID 70158280Ethyl 2-acetoxymethyl-4-(3-chlorophenyl)-6-methyl-5-(3-phenyl-2-propene-1-ylcarbamoyl)-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
120 °C

Procedure

652 mg (3.00 mmol) of 3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 0.510 ml (3.00 mmol) of 3-chlorobenzaldehyde and 0.045 ml (0.30 mmol) of piperidine were heated under reflux in 37.5 ml of benzene overnight while water was removed. The reaction solution was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue thus obtained, 564 mg (3.0 mmol) of ethyl 4-acetoxy-3-oxobutyrate and 278 mg (3.6 mmol) of ammonium acetate were heated at 80° C. under stirring in 15 ml of 2-propanol for four nights. The reaction mixture was then heated at 120° C. under stirring under atmospheric pressure for 4 hours while 2-propanol was evaporated. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/2) to obtain the title compound.

Workup

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

Sources & evidence

ORD record
ord-41a7643709914e13bef254f4c94c4da6
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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