Sodium Chloride → HCID 54043378, compound

HRID 1389531Notes

Reaction equation

HRID 1389531 reaction equation
[C:1]1([CH:7]=[CH:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16]([NH2:18])=O)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.[Cl-].[Na+].[OH-].[Na+]>ClCCCl>[C:1]1([CH:7]=[CH:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16]#[N:18])[CH2:12][CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 3919551HCID 3919551, compound

Product 1

HCID 54043378HCID 54043378, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 99.4 g of the 1-(3-phenyl-2-propenyl)-4-piperidinecarboxamide, 25 ml of phosphorus oxychloride and 30 g of sodium chloride are suspended in 750 ml of 1,2-dichloroethane and heated to its reflux temperature with vigorous stirring for a period of 2 hours. After several minutes at the reflux temperature a white precipitate separates. The reaction mixture is cooled, a 10% sodium hydroxide solution is added and the mixture extracted with diethyl ether. The combined extracts are washed with water, followed by a solution of sodium chloride, dried (MgSO4) and concentrated in vacuo. The residual oil is distilled under reduced pressure to yield the desired 1-(3-phenyl-2-propenyl)-4-piperidinecarbonitrile as a viscous, colorless oil, b.p. 169°-76° C./0.35-0.70 mm.

Workup

  1. temperatureheated to its
  2. temperaturereflux temperature
  3. waitAfter several minutes at the reflux temperature a white precipitate separates
  4. temperatureThe reaction mixture is cooled
  5. extractionthe mixture extracted with diethyl ether
  6. washThe combined extracts are washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. distillationThe residual oil is distilled under reduced pressure

Sources & evidence

ORD record
ord-39c6ec15d4d8410385b85c8ca1eaf097
Source dataset
uspto-grants-1981_01
Patent number
US04244955

Reaction notes

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