Benzene, (3-chloro-1-propenyl)- → HCID 70620984, compound

HRID 1657783Notes

Reaction equation

HRID 1657783 reaction equation
[C:1]([CH:3]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)#[N:2].[CH2:20]([Cl:29])[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1C=CC=CC=1>[ClH:29].[ClH:29].[C:1]([CH:3]([N:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH:21]=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:19]1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)#[N:2]

Participants

4

Reactant 2

HCID 94242Benzene, (3-chloro-1-propenyl)-HCID 21388458HCID 21388458, compound

Product 1

HCID 70620984HCID 70620984, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To 3.6 g. of N-(α-cyano-3,4-dimethoxybenzyl)piperazine was added 8 ml. of benzene and then 1.47 g. of soda ash. To the resulting mixture was added 2.53 g. of cinnamyl chloride over a period of about 1 hour while the mixture was heated under reflux with stirring. After dropping, the mixture was further refluxed with stirring for 2 hours. After cooling, the mixture was filtered and the filtrate was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure. To the residue was added ligroin to be allowed to stand to give crystal which was collected by filtration. The product was recrystallized from ligroin to give 3.4 g. of crystal having a melting point of 119° - 123°C. This crystal was dissolved in benzene and the resultant solution was saturated with dry hydrochloric gas to separate crystal which was collected by filtration. Recrystallization from methanol afforded N-(α-cyano-3,4-dimethoxybenzyl)-N'-cinnamyl piperazine dihydrochloride as needles melting at 203° - 204.6°C. (decomposition).

Workup

  1. additionTo the resulting mixture was added 2.53 g
  2. temperatureunder reflux
  3. temperaturethe mixture was further refluxed
  4. stirringwith stirring for 2 hours
  5. temperatureAfter cooling
  6. filtrationthe mixture was filtered
  7. washthe filtrate was washed with water
  8. dry with materialdried over sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. additionTo the residue was added ligroin
  11. customto give crystal which
  12. filtrationwas collected by filtration
  13. customThe product was recrystallized from ligroin
  14. customto give 3.4 g
  15. customwith dry hydrochloric gas
  16. customto separate crystal which
  17. filtrationwas collected by filtration
  18. customRecrystallization from methanol

Sources & evidence

ORD record
ord-fea43e5d5f6749bba87cf8f5d6a0e67b
Source dataset
uspto-grants-1976_06
Patent number
US03962247

Reaction notes

Loading…