Piperazine → HCID 67575246, compound

HRID 342495Notes

Reaction equation

HRID 342495 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][C:21](OC)=[O:22])=[C:10]1[C:25]([O:27][CH3:28])=[O:26].[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.CN(C)C=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][C:21]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:22])=[C:10]1[C:25]([O:27][CH3:28])=[O:26]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 6228DimethylformamideHCID 67574494HCID 67574494, compound

Product 1

HCID 67575246HCID 67575246, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of dimethyl 4-(2,6-dichlorophenyl)-2-methoxycarbonylmethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate(13.9 g, 30 mmol) , piperazine(39.2 g, 460 mmol), and dimethylformamide(30 ml) was heated to 100° C. (becomes a solution) and stirred for 1.5 h (longer reaction times result in decomposition). The reaction mixture was cooled briefly, poured into water(800 ml), and extracted with ethyl acetate. The extract was washed thoroughly with water, dried over sodium sulfate, and concentrated to give 12.2 g (84%) of an orange color oil, suitable for use in succeeding steps. It can be purified by column chromatography on silica gel using dichloromethane/methanol: 2/1 as eluent.

Workup

  1. customlonger reaction times
  2. customresult in decomposition)
  3. temperatureThe reaction mixture was cooled briefly
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed thoroughly with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give 12.2 g (84%) of an orange color oil
  9. customIt can be purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b3afd91975ac471aac79999622964cc9
Source dataset
uspto-grants-1999_01
Patent number
US05859011

Reaction notes

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