Piperidine → Methyl 3-(1-(2-acetylaminoethyl)-2,5-dimethylpyrrol-3-yl)-2propenoate

HRID 1089432Notes

Reaction equation

HRID 1089432 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([O-])=O.[C:9]([NH:12][CH2:13][CH2:14][N:15]1[C:19]([CH3:20])=[CH:18][C:17](C=O)=[C:16]1[CH3:23])(=[O:11])[CH3:10].N1CCCCC1>N1C=CC=CC=1>[C:9]([NH:12][CH2:13][CH2:14][N:15]1[C:16]([CH3:23])=[CH:17][C:18]([CH:3]=[CH:2][C:1]([O:7][CH3:8])=[O:6])=[C:19]1[CH3:20])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 178134N-(2-(3-Formyl-2,5-dimethyl-1H-pyrrol-1-yl)ethyl)acetamideHCID 3801157Monomethyl malonate2×

Product 1

HCID 53938375Methyl 3-(1-(2-acetylaminoethyl)-2,5-dimethylpyrrol-3-yl)-2propenoateYield 56.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6.1 g (0.05 mol) of monomethyl malonate are dissolved in 20 ml of pyridine. After addition of 10.4 g (0.05 mol) of 1-(2-acetylaminoethyl)-2,5-dimethylpyrrole-3-aldehyde (see Example 13) and 1 ml of piperidine, the mixture is heated under reflux for 15 hours. After addition of a further 27 g of monomethyl malonate, heating is continued for a further 24 hours, the mixture is concentrated, the residue is taken up in water, the mixture is extracted with methylene chloride and the methylene chloride phase is washed with dilute acid and alkali and concentrated. Column chromatography with methylene chloride:methanol=98:2 as the mobile phase gives 7.5 g of product, which can be recrystallized from ethyl acetate.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 15 hours
  3. temperatureheating
  4. concentrationthe mixture is concentrated
  5. extractionthe mixture is extracted with methylene chloride
  6. washthe methylene chloride phase is washed
  7. additionwith dilute acid
  8. concentrationalkali and concentrated

Sources & evidence

ORD record
ord-02c9651e9d414fd2b76b877bd5afd129
Source dataset
uspto-grants-1990_10
Patent number
US04966901

Reaction notes

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