Acetonitrile → HCID 20187494, compound

HRID 2308757Notes

Reaction equation

HRID 2308757 reaction equation
Br[CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[CH:6]=1)=[O:4].C(#N)C.[CH2:17]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)C>[CH2:17]([CH:24]1[CH2:29][CH2:28][N:27]([CH:2]([CH3:13])[C:3]([C:5]2[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[CH:6]=2)=[O:4])[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 317384-BenzylpiperidineHCID 20187481HCID 20187481, compound

Product 1

HCID 20187494HCID 20187494, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

21 g of 2-bromo-3'-,5'-dimethylpropiophenone are introduced into 50 ml of acetonitrile, the mixture is cooled to 0° C., 30.5 g of 4-benzylpiperidine are added and the mixture is stirred for 3 hours. It is diluted with 30 ml of diethyl ether, the precipitated hydrobromide is filtered off and 150 ml of diethyl ether are added to the filtrate, which produces a second crop of precipitate. This is filtered off and the filtrate is treated twice with 200 ml of 3N hydrochloric acid. The diethyl ether phase is separated off. The aqueous phase contains the hydrochloride of the propiophenone formed, as an emulsion. This aqueous phase is extracted with methylene chloride, the organic phase obtained is washed with water, dilute aqueous ammonia solution is added, the organic phase is decanted, washed with water, dried, filtered and treated with 100 g of silica, the mixture is filtered and the filtrate is evaporated. 14.4 g of an oil remain.

Workup

  1. filtrationthe precipitated hydrobromide is filtered off
  2. addition150 ml of diethyl ether are added to the filtrate, which
  3. customproduces a second crop of precipitate
  4. filtrationThis is filtered off
  5. additionthe filtrate is treated twice with 200 ml of 3N hydrochloric acid
  6. customThe diethyl ether phase is separated off
  7. customformed, as an emulsion
  8. extractionThis aqueous phase is extracted with methylene chloride
  9. customthe organic phase obtained
  10. washis washed with water, dilute aqueous ammonia solution
  11. additionis added
  12. customthe organic phase is decanted
  13. washwashed with water
  14. customdried
  15. filtrationfiltered
  16. additiontreated with 100 g of silica
  17. filtrationthe mixture is filtered
  18. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-8d3798cc60c9498db80ed06035fe512c
Source dataset
uspto-grants-1987_09
Patent number
US04690931

Reaction notes

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