Dimethylformamide → HCID 70044275, compound

HRID 544249Notes

Reaction equation

HRID 544249 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:9]([C:20]([OH:22])=[O:21])=[C:8]([CH3:23])[NH:7][C:6]=1[CH3:24])=[O:4].[CH3:25]N(C)C=O.S(Cl)([Cl:32])=O.[C:34]1([CH:40]([N:42]2[CH2:47][CH2:46][CH:45](O)[CH2:44][CH2:43]2)C)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCl>[ClH:32].[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:9]([C:20]([O:22][CH:45]2[CH2:44][CH2:43][N:42]([CH2:40][CH2:34][C:39]3[CH:25]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:47][CH2:46]2)=[O:21])=[C:8]([CH3:23])[NH:7][C:6]=1[CH3:24])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl esterHCID 2840181HCID 2840181, compound

Product 1

HCID 70044275HCID 70044275, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In this example, 4.98 g of 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester was suspended in a mixture solvent of 7.5 ml of dimethylformamide and 30 ml of dichloromethane, and 1.2 ml of thionyl chloride was added thereto under ice cooling. The mixture was stirred under ice cooling for 1.5 hours to make a homogeneous solution. 3.39 g of 1-(1-phenylethyl)-4-hydroxypiperidine was added thereto, and then stirring was effected under ice cooling for 2 hours. After completion of the reaction, the reaction mixture was washed with an aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, and the concentrated under reduced pressure. The desired product was separated by silica gel column chromatography (eluent:chloroform:methanol=20:1 v/v). The fractions containing the desired product was treated similarly as in Example 2 to obtain 3.44 g of yellow 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-[1-(-phenylethyl)-4-piperidinyl]ester-5-methyl ester hydrochloride (recrystallization solvent: aceton-ethyl acetate) [compound of the general formula (I) wherein R1 =R2 =R4 =CH3, ##STR22## wherein n=0, ##STR23## (yield: 41.2%)

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas effected under ice cooling for 2 hours
  4. customAfter completion of the reaction
  5. washthe reaction mixture was washed with an aqueous sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationthe concentrated under reduced pressure
  8. customThe desired product was separated by silica gel column chromatography (eluent:chloroform:methanol=20:1 v/v)
  9. additionThe fractions containing the desired product
  10. additionwas treated similarly as in Example 2

Sources & evidence

ORD record
ord-96f4b7750bd74bfb868fd974feb1f5d1
Source dataset
uspto-grants-1984_05
Patent number
US04448964

Reaction notes

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