Piperidine → 3-(3-Phenyl-2-propene-1-yl) 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-dimethoxylmethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 890149Notes

Reaction equation

HRID 890149 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4](=O)[CH2:5][C:6]([O:8][CH2:9][CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O.N1CCCCC1.[NH2:36]/[C:37](/[CH3:46])=[CH:38]\[C:39]([O:41][CH2:42][CH2:43][C:44]#[N:45])=[O:40]>C1C=CC=CC=1.CC(O)C.O>[Cl:21][C:22]1[CH:23]=[C:24]([CH:25]2[C:38]([C:39]([O:41][CH2:42][CH2:43][C:44]#[N:45])=[O:40])=[C:37]([CH3:46])[NH:36][C:4]([CH:3]([O:19][CH3:20])[O:2][CH3:1])=[C:5]2[C:6]([O:8][CH2:9][CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:7])[CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 136714102-Cyanoethyl 3-aminocrotonateHCID 53702825(3-Phenyl-2-propene-1-yl) 4,4-dimethoxy-3-oxobutyrate

Product 1

HCID 695899473-(3-Phenyl-2-propene-1-yl) 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-dimethoxylmethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

2.09 g (7.5 mmol) of (3-phenyl-2-propene-1-yl) 4,4-dimethoxy-3-oxobutyrate, 0.85 ml (7.5 mmol) of 3-chlorobenzaldehyde and 0.1 ml of piperidine were heated under reflux in 7.5 ml of benzene overnight while water was removed. The reaction liquid was washed was water and dried over anhydrous sodium sulfate. The solvent was distilled under reduced pressure, and the residue was heated together with 1.16 g (7.5 mmol) of 2-cyanoethyl 3-aminocrotonate at 70° C. in 37.5 ml of 2-propanol under stirring for four nights. The heating and stirring were continued at 120° C. overnight while 2-propanol was evaporated under atmospheric pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1) to obtain the title compound.

Workup

  1. customwas removed
  2. customThe reaction liquid
  3. washwas washed
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled under reduced pressure
  6. stirringThe heating and stirring
  7. customwas evaporated under atmospheric pressure
  8. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-4584127520f54477adeb76b555f11b79
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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