Piperidine → 2-Cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-(methyl-(3-phenyl-2-propene-1-yl)carbamoyl)-1,4-dihydropyridine-3-carboxylate

HRID 1700339Notes

Reaction equation

HRID 1700339 reaction equation
[CH3:1][N:2]([CH2:9][CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3](=[O:8])[CH2:4][C:5](=O)[CH3:6].[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O.N1CCCCC1.[NH2:33]/[C:34](/[CH3:43])=[CH:35]\[C:36]([O:38][CH2:39][CH2:40][C:41]#[N:42])=[O:37]>CC(O)C.O>[Cl:18][C:19]1[CH:20]=[C:21]([CH:22]2[C:4]([C:3](=[O:8])[N:2]([CH3:1])[CH2:9][CH:10]=[CH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:5]([CH3:6])[NH:33][C:34]([CH3:43])=[C:35]2[C:36]([O:38][CH2:39][CH2:40][C:41]#[N:42])=[O:37])[CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 136714102-Cyanoethyl 3-aminocrotonateHCID 53834343N-methyl-3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide

Product 1

HCID 701564182-Cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-(methyl-(3-phenyl-2-propene-1-yl)carbamoyl)-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
120 °C

Procedure

306 mg (1.32 mmol) of N-methyl-3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 0.150 ml (1.32 mmol) of 3-chlorobenzaldehyde and 0.013 ml (0.132 mmol) of piperidine were heated under reflux overnight while water was removed. After washing with water, the organic layer was dried over anhydrous magnesium sulfate and then the solvent was evaporated under reduced pressure. The residue and 204 mg (1.32 mmol) of 2-cyanoethyl 3-aminocrotonate were heated at 85° C. under stirring in 6.6 ml of 2-propanol overnight. The reaction mixture was further heated at 120° C. under stirring under atmospheric pressure for 3 hours while 2-propanol was evaporated. The residue was purified by the high-performance liquid chromatography to obtain the title compound.

Workup

  1. customwas removed
  2. washAfter washing with water
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customwas evaporated
  6. customThe residue was purified by the high-performance liquid chromatography

Sources & evidence

ORD record
ord-82e8023be53c4d19bfac6f1781666ad6
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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