Pyrrolidine → HCID 19890890, compound

HRID 893626Notes

Reaction equation

HRID 893626 reaction equation
Cl.Cl[CH:3]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7][CH2:6][CH2:5][CH2:4]1.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>O>[N:14]1([CH:3]2[C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:8]3[CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 19890891HCID 19890891, compound

Product 1

HCID 19890890HCID 19890890, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 g of 9-chloro-6,7,8,9-tetrahydro-5H -cyclohepta[b]pyridine hydrochloride were dissolved in 12.5 ml of water and 8 ml of pyrrolidine were added. The mixture was refluxed with vigorous stirring for 5 hours and the excess pyrrolidine was evaporated off under reduced pressure. 25 ml of a saturated solution of sodium bicarbonate and then 50 ml of water were added followed by extraction with methylene chloride. The combined organic phases were washed with water, dried and concentrated to dryness under reduced pressure. The residue was chromatographed on silica and eluted with a mixture of methylene chloride and methanol (9-1) to obtain 2.25 g of the expected product with an Rf=0.20. 2.25 g of the product were crystallized from petroleum ether (b.p. 40°-70° C.) to obtain 2 g of the expected product melting about 62° C.

Workup

  1. temperatureThe mixture was refluxed
  2. customthe excess pyrrolidine was evaporated off under reduced pressure
  3. addition25 ml of a saturated solution of sodium bicarbonate and then 50 ml of water were added
  4. extractionfollowed by extraction with methylene chloride
  5. washThe combined organic phases were washed with water
  6. customdried
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue was chromatographed on silica
  9. washeluted with a mixture of methylene chloride and methanol (9-1)

Sources & evidence

ORD record
ord-121f2c13a3d843ca9ce36c59f50022d5
Source dataset
uspto-grants-1992_06
Patent number
US05126353

Reaction notes

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