N-methyl-2-pyrrolidone → HCID 178447988, compound

HRID 564671Notes

Reaction equation

HRID 564671 reaction equation
C[N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.[CH2:8]([C@H:11]1[CH2:16][CH2:15][C@H](C=CBr)[CH2:13][CH2:12]1)[CH2:9][CH3:10].[Cu](C#N)C#N>Cl>[CH2:8]([C@H:11]1[CH2:16][CH2:15][C@H:6]([CH:5]=[CH:4][C:3]#[N:2])[CH2:13][CH2:12]1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 178418260HCID 178418260, compoundHCID 178447938HCID 178447938, compound

Product 1

HCID 178447988HCID 178447988, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 30 ml of N-methylpyrrolidone was dissolved 3 g of 2-(trans-4-propylcyclohexyl)ethenyl bromide, 2 g of copper cyanide was added thereto, and then stirred under reflux by heating for 7 hours. A solution of ferric chloride in 6N hydrochloric acid was added to the reaction liquid, and extracted with toluene. The organic layer thus obtained was washed with water, dried, and then concentrated under a reduced pressure to obtain a brown oily product. This product was isolated and purified by using silica gel column chromatography to obtain 1.5 g of an oily product. As a result of various instrumental analysises, the product was confirmed to be the subject compound.

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. temperatureby heating for 7 hours
  4. extractionextracted with toluene
  5. customThe organic layer thus obtained
  6. washwas washed with water
  7. customdried
  8. concentrationconcentrated under a reduced pressure
  9. customto obtain a brown oily product
  10. customThis product was isolated
  11. custompurified

Sources & evidence

ORD record
ord-574ac1b8ab2e4ef1a751a2914dbc0520
Source dataset
uspto-grants-2001_01
Patent number
US06168839A

Reaction notes

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