Water → HCID 3919551, compound

HRID 1389530Notes

Reaction equation

HRID 1389530 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.Cl[CH2:11][CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[K+].O>C1(C)C=CC=CC=1>[C:14]1([CH:13]=[CH:12][CH2:11][N:1]2[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 37724-PiperidinecarboxamideHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 516893Potassium Bicarbonate

Product 1

HCID 3919551HCID 3919551, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 60.0 g of isonipecotamide (4-piperidinecarboxamide), 75.0 g of (3-chloropropenyl)benzene and 72 g of potassium acid carbonate suspended in 700 ml of toluene are heated with stirring at their reflux temperature for a period of 4 hours. The reaction mixture is cooled, water added thereto and filtered. The crude product is washed with water, ether and recrystallized from a 5:1 ethanol/water mixture to yield 99.4 g of 1-(3-phenyl-2-propenyl)-4-piperidinecarboxamide as light beige needles having a m.pt. of 189.5°-191.5° C.

Workup

  1. temperatureare heated
  2. temperaturereflux temperature for a period of 4 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. washThe crude product is washed with water, ether
  6. customrecrystallized from a 5:1 ethanol/water mixture

Sources & evidence

ORD record
ord-2f3ed333c36c48b4aafaed6b497389ce
Source dataset
uspto-grants-1981_01
Patent number
US04244955

Reaction notes

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