Methanol → HCID 21388463, compound

HRID 1657781Notes

Reaction equation

HRID 1657781 reaction equation
C(C(N1CCNCC1)C1C=CC(OC)=CC=1)#N.CO.[Cl:20]C(OCC)=O.[C:26]([CH:28]([N:37]1[CH2:42][CH2:41][N:40]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:39][CH2:38]1)[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)#[N:27]>C1C=CC=CC=1>[ClH:20].[C:26]([CH:28]([N:37]1[CH2:42][CH2:41][N:40]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:39][CH2:38]1)[C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)#[N:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 10928Ethyl chloroformateHCID 16226924HCID 16226924, compoundHCID 21388449HCID 21388449, compound

Product 1

HCID 21388463HCID 21388463, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 100-ml. three necked flask was placed 11.5 g. of N-(α-cyano-4-methoxybenzyl)piperazine and 40 ml. of methanol to obtain a homogenous solution. To the resulting solution was added dropwise 5.96 g. of ethyl chloroformate over a period of about 70 minutes with stirring while the temperature was kept at about 20°C. After dropping, the internal temperature was raised to 40° to 45°C., and then the mixture was further stirred for 2 hours. The solution was concentrated under reduced pressure and 500 ml. of water was added thereto. This solution was made alkaline with the aid of sodium carbonate with cooling and extracted with benzene. The benzene layer was washed with dilute hydrochloric acid and water, and dried over sodium sulfate. The solvent was distilled off to afford 9.7 g. of N-(α-cyano-4-methoxybenzyl)-N'-ethoxycarbonylpiperazine as an oily substance. This product was dissolved in benzene and the resultant solution was saturated with dry hydrochloric gas to separate crystal which was collected by filtration. Recrystallization from acetone afforded N-(α-cyano-4-methoxybenzyl)-N' -ethoxycarbonylpiperazine hydrochloride having a melting point of 170°C.

Workup

  1. additionTo the resulting solution was added dropwise 5.96 g
  2. customwas kept at about 20°C
  3. temperaturethe internal temperature was raised to 40° to 45°C.
  4. concentrationThe solution was concentrated under reduced pressure and 500 ml
  5. additionof water was added
  6. temperaturewith cooling
  7. extractionextracted with benzene
  8. washThe benzene layer was washed with dilute hydrochloric acid and water
  9. dry with materialdried over sodium sulfate
  10. distillationThe solvent was distilled off
  11. customto afford 9.7 g
  12. customwith dry hydrochloric gas
  13. customto separate crystal which
  14. filtrationwas collected by filtration
  15. customRecrystallization from acetone

Sources & evidence

ORD record
ord-b3a2ff5683cc49a6be8d9a88809de6c1
Source dataset
uspto-grants-1976_06
Patent number
US03962247

Reaction notes

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