Pyrrolidine → HCID 14327173, compound

HRID 1651076Notes

Reaction equation

HRID 1651076 reaction equation
Cl.Cl[CH:3]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4]1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>O>[N:12]1([CH:3]2[C:11]3[N:10]=[CH:9][CH:8]=[CH:7][C:6]=3[CH2:5][CH2:4]2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 19890889HCID 19890889, compound

Product 1

HCID 14327173HCID 14327173, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 g of 7-chloro-6,7-dihydro-5H-1-pyrindine hydrochloride were dissolved in 10 ml of water and 8.8 ml of pyrrolidine were added, followed by stirring for two-and-a-half hours at ambient temperature. Extraction was done with methylene chloride and the extracts were washed with water, dried and concentrated to dryness under reduced pressure. The residue was taken up in ethyl acetate, treated with active charcoal, filtered and taken to dryness under reduced pressure. The residue was chromatographed on silica and eluted with a mixture of ethyl acetate and triethylamine (95-5) to obtain 4.71 g of the expected product.

Workup

  1. extractionExtraction
  2. washthe extracts were washed with water
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure
  5. additiontreated with active charcoal
  6. filtrationfiltered
  7. customThe residue was chromatographed on silica
  8. washeluted with a mixture of ethyl acetate and triethylamine (95-5)

Sources & evidence

ORD record
ord-dcbca0d3b2d54f29988948742df5854b
Source dataset
uspto-grants-1990_05
Patent number
US04927832

Reaction notes

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