Hydrochloric Acid → HCID 21388463, compound

HRID 1657779Notes

Reaction equation

HRID 1657779 reaction equation
C(OC(N1CCNCC1)=O)C.[ClH:12].COC1C=CC(C=O)=CC=1.[C-]#N.[Na+].[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.O.CO>[ClH:12].[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

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8929Sodium CyanideHCID 312444-MethoxybenzaldehydeHCID 21388449HCID 21388449, compound

Product 1

HCID 21388463HCID 21388463, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To the mixture of 12.8 g. of N-ethoxycarbonylpiperazine, 13 ml. of water and 7.1 ml. of 35 % hydrochloric acid was added dropwise 10 g. of 4-methoxybenzaldehyde in 40 ml. of methanol at 5° to 10°C. over a period of 5 minutes, and then 3.96 g. of sodium cyanide in 10 ml. of water was added thereto dropwise with stirring at the same temperature over a period of about 30 minutes. The resulting mixture was stirred at 40°C. for 2 hours, and a completion of the reaction was confirmed by means of Thin-Layer chromatography. Solvent was evaporated, and the resultant was dissolved in benzene, washed with diluted hydrochloric acid and water, and then dried over sodium sulfate. Benzene was evaporated to give 19.5 g. of N-(α-cyano-4-methoxybenzyl)-N'-ethoxycarbonylpiperazine as an oily substance. The oil was dissolved in benzene, and dry hydrochloric acid gas was saturated therein, and then separated crystals were collected by filtration, recrystallized from acetone to give N-(α-cyano-4-methoxybenzyl)-N'-ethoxycarbonylpiperazine hydrochloride having a melting point of 170°C.

Workup

  1. additionTo the mixture of 12.8 g
  2. stirringThe resulting mixture was stirred at 40°C. for 2 hours
  3. customSolvent was evaporated
  4. dissolutionthe resultant was dissolved in benzene
  5. washwashed with diluted hydrochloric acid and water
  6. dry with materialdried over sodium sulfate
  7. customBenzene was evaporated
  8. customto give 19.5 g
  9. customseparated crystals
  10. filtrationwere collected by filtration
  11. customrecrystallized from acetone

Sources & evidence

ORD record
ord-e5d76003a74d48769244265d2816ac4e
Source dataset
uspto-grants-1976_06
Patent number
US03962247

Reaction notes

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