1,8-Diazabicyclo(5.4.0)undec-7-ene → 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 2-[4-(2-thenoyl)-piperidino]-ethyl ester hydrochloride

HRID 1721894Notes

Reaction equation

HRID 1721894 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]([C:7]1[CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:9]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([CH3:14])[NH:11][C:12]=1[CH3:13])=[O:6].[C:28]1([C:33]([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[O:34])[S:32][CH:31]=[CH:30][CH:29]=1.N12CCCN=C1CCCCC2>C(OCC)(=O)C>[ClH:1].[C:28]1([C:33]([CH:35]2[CH2:36][CH2:37][N:38]([CH2:2][CH2:3][O:4][C:5]([C:7]3[CH:8]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=4)[C:9]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([CH3:14])[NH:11][C:12]=3[CH3:13])=[O:6])[CH2:39][CH2:40]2)=[O:34])[S:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 30168882-Chloroethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylateHCID 15337453(Piperidin-4-yl)(thiophen-2-yl)methanone

Product 1

HCID 703945152,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 2-[4-(2-thenoyl)-piperidino]-ethyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 11 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 2-chloroethyl ester, 6.4 g of 4-(2-thenoyl)-piperidine and 8.8 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene is stirred under argon for 1 hour in a bath at 150°. After cooling, the melt is dissolved in 100 ml of ethyl acetate and the solution is washed three times with 1N hydrochloric acid. The aqueous-acidic solution is adjusted to pH 9-10 with 50% potassium carbonate solution and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and concentrated by evaporation and the residue is dissolved in ether. By the addition of a solution of hydrogen chloride in ether there is obtained 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 2-[4-(2-thenoyl)-piperidino]-ethyl ester hydrochloride which melts at 140°-145°; it sinters from 120°.

Workup

  1. temperatureAfter cooling
  2. washthe solution is washed three times with 1N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. dissolutionthe residue is dissolved in ether
  7. additionBy the addition of a solution of hydrogen chloride in ether

Sources & evidence

ORD record
ord-ad80e00f6ae4460c978730fe62beb544
Source dataset
uspto-grants-1989_08
Patent number
US04853393

Reaction notes

Loading…