3-Nitrobenzaldehyde → HCID 20230104, compound

HRID 2290726Notes

Reaction equation

HRID 2290726 reaction equation
[C:1]([O:7][CH:8]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=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+:21]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O)([O-:23])=[O:22].[NH2:32]/[C:33](/[CH3:39])=[CH:34]\[C:35]([O:37][CH3:38])=[O:36]>C(O)(C)C>[S:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[CH:8]([O:7][C:1]([C:2]1[CH:27]([C:26]2[CH:29]=[CH:30][CH:31]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=2)[C:34]([C:35]([O:37][CH3:38])=[O:36])=[C:33]([CH3:39])[NH:32][C:3]=1[CH3:5])=[O:6])[CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 54149542HCID 54149542, compound

Product 1

HCID 20230104HCID 20230104, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In 350 ml of isopropanol are dissolved 30.9 g of 1-(2-thienyl)-2-piperidinoethyl acetoacetate, 15.4 g of m-nitrobenzaldehyde and 11.7 g of methyl β-aminocrotonate, and the mixture is refluxed under heating for 20 hours. The reaction mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel (eluent:chloroform:methanol=10:1.2 (by volume)). The firstly eluted solution is concentrated and recrystallized from ethanol to give 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-[1-(2-thienyl)-2-piperidinoethyl]ester as crystals melting at 179° C.-181° C. This is α-diastereoisomer and the hydrochloride therefore melts at 215° C.-218° C. (decomposition). The lastly eluted solution is concentrated and recrystallized from ethanol as crystals melting at 128° C.-134° C. The hydrochloride thereof melts at 188° C.-190° C. (decomposition).

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating for 20 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customthe residue is purified by column chromatography on silica gel (eluent:chloroform:methanol=10:1.2 (by volume))
  5. concentrationThe firstly eluted solution is concentrated
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-cb9eeec479d74ce697c33a03e10cd64e
Source dataset
uspto-grants-1986_10
Patent number
US04618607

Reaction notes

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