Ammonia → 3-cyclopropylmethyl 5-[2-(N-benzyl-N-methylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 621537Notes

Reaction equation

HRID 621537 reaction equation
[C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:19]([C:22]1[CH:23]=[C:24]([CH:37]=[CH:38][CH:39]=1)[CH:25]=[C:26]([C:34]([CH3:36])=O)[C:27]([O:29][CH2:30][CH:31]1[CH2:33][CH2:32]1)=[O:28])([O-:21])=[O:20].[NH3:40]>C(O)C>[CH3:36][C:34]1[NH:40][C:3]([CH3:5])=[C:2]([C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:11])=[O:6])[CH:25]([C:24]2[CH:37]=[CH:38][CH:39]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:26]=1[C:27]([O:29][CH2:30][CH:31]1[CH2:33][CH2:32]1)=[O:28]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 117768292-[Methyl(phenylmethyl)amino]ethyl 3-oxobutanoateHCID 53956239Cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate

Product 1

HCID 30659143-cyclopropylmethyl 5-[2-(N-benzyl-N-methylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylateYield 42.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.0 g (16 mmol) of 2-(N-benzyl-N-methylamino)ethyl acetoacetate, 4.6 g (16 mmol) of cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate, 1.12 ml of 28% aqueous ammonia and 40 ml of ethanol was stirred at the reflux temperature for 8 hours, and then the solvent was removed under reduced pressure. The residue was chromatographed on silica gel column to afford 3-cyclopropylmethyl 5-[2-(N-benzyl-N-methylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (3.5 g, 42.1%) as yellow oil. Treatment of this oil with hydrochloric acid gave the corresponding salt.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-54e3911edb1240338130292957529339
Source dataset
uspto-grants-1989_04
Patent number
US04824855

Reaction notes

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