3-Nitrobenzaldehyde → HCID 20230121, compound

HRID 2290725Notes

Reaction equation

HRID 2290725 reaction equation
[C:1]([O:7][CH:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:22]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=O)([O-:24])=[O:23].[NH2:33]/[C:34](/[CH3:40])=[CH:35]\[C:36]([O:38][CH3:39])=[O:37]>C(O)(C)C>[C:16]1([CH:8]([O:7][C:1]([C:2]2[CH:28]([C:27]3[CH:30]=[CH:31][CH:32]=[C:25]([N+:22]([O-:24])=[O:23])[CH:26]=3)[C:35]([C:36]([O:38][CH3:39])=[O:37])=[C:34]([CH3:40])[NH:33][C:3]=2[CH3:5])=[O:6])[CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 13909610HCID 13909610, compound

Product 1

HCID 20230121HCID 20230121, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In 300 ml of isopropanol are dissolved 28.9 g of 1-phenyl-2-piperidinoethyl acetoacetate, 15.1 g of m-nitrobenzaldehyde and 11.5 g of methyl β-aminocrotonate, and the mixture is refluxed under heating for 17 hours. The reaction mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel (eluent:chloroform:methanol=10:1 (by volume)). The eluate containing the object compound is concentrated and recrystallized from isopropanol to give 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-(1-phenyl-2-piperidinoethyl)ester as crystals melting at 183°-185° C. (decomposition). This is α-diastereoisomer. The hydrochloride thereof melts at 238°-240° C. (decomposition). The β-diastereoisomer which can be obtained in similar manner melts at 127°-130° C. (from isopropanol), and the hydrochloride thereof melts at 222°-223° C. (decomposition) (from ethanol).

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating for 17 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customthe residue is purified by column chromatography on silica gel (eluent:chloroform:methanol=10:1 (by volume))
  5. additionThe eluate containing the object compound
  6. concentrationis concentrated
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-f346b8641b114a428df8b350819db828
Source dataset
uspto-grants-1986_10
Patent number
US04618607

Reaction notes

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