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Ethyl chloroformate → HCID 21388470, compound

HRID 1657782
Notes
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Reaction equation

HRID 1657782 reaction equation
C(C(N1CCNCC1)C1C=CC([Cl:10])=CC=1)#N.C(=O)([O-])[O-].[K+].[K+].ClC(OCC)=O.[C:29]([CH:31]([N:39]1[CH2:44][CH2:43][N:42]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:41][CH2:40]1)[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)#[N:30]>C1C=CC=CC=1.O>[ClH:10].[C:29]([CH:31]([N:39]1[CH2:44][CH2:43][N:42]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:41][CH2:40]1)[C:32]1[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=1)#[N:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 21388465α-(4-Chlorophenyl)-1-piperazineacetonitrileHCID 21388468HCID 21388468, compound

Product 1

HCID 21388470HCID 21388470, compound

Reagents, catalysts & solvents 2

HCID 241
Benzene
Solvent
3×
HCID 962WaterSolvent

Procedure

To 11.7 g. of N-(α-cyano-4-chlorobenzyl)piperazine was added 70 ml. of benzene and then 6.9 g. of anhydrous potassium carbonate. To the resulting solution was added dropwise 5.4 g. of ethyl chloroformate dissolved in 30 ml. of benzene with cooling. After dropping, the mixture was stirred for 2 hours at 40° - 45°C. After cooling, water was poured into the mixture to dissolve inorganic substance. The benzene layer was separated, washed with water, dried over sodium sulfate, and the solvent distilled off. There was obtained 10.7 g. of N-(α-cyano-4-chlorobenzyl)-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-chlorobenzyl)-N'-ethoxycarbonylpiperazine hydrochloride having a melting point of 166°C.

Workup

  1. additionTo the resulting solution was added dropwise 5.4 g
  2. temperatureAfter cooling
  3. dissolutionto dissolve inorganic substance
  4. customThe benzene layer was separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. distillationthe solvent distilled off
  8. customThere was obtained 10.7 g
  9. customwith dry hydrochloric gas
  10. customto separate crystal which
  11. filtrationwas collected by filtration
  12. customRecrystallization from acetone

Sources & evidence

ORD record
ord-5c62f18cb82d4f0f9db43bec1d5e405a
Source dataset
uspto-grants-1976_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03962247

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes