Pyrrolidine → HCID 14327173, compound

HRID 893624Notes

Reaction equation

HRID 893624 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-3af90a411b414460b9a3675adc1ee0f0
Source dataset
uspto-grants-1992_06
Patent number
US05126353

Reaction notes

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