1-Chloroethyl chloroformate → 4-[(2S,5R)-2,5-Dimethylpiperazin-1-yl]-2-methylbenzonitrile

HRID 1593374Notes

Reaction equation

HRID 1593374 reaction equation
C([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH3:23])[CH:16]=2)[C@@H:10]([CH3:24])[CH2:9]1)C1C=CC=CC=1.C(Cl)(=O)OC(Cl)C>ClC(Cl)C>[CH3:24][C@H:10]1[CH2:9][NH:8][C@H:13]([CH3:14])[CH2:12][N:11]1[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([CH3:23])[CH:16]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 686953104-[(2S,5R)-4-benzyl-2,5-dimethylpiperazin-1-yl]-2-methylbenzonitrile

Product 1

HCID 686963004-[(2S,5R)-2,5-Dimethylpiperazin-1-yl]-2-methylbenzonitrileYield 85.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Into 50 ml of dichloroethane was dissolved 1.81 g of 4-[(2S,5R)-4-benzyl-2,5-dimethylpiperazin-1-yl]-2-methylbenzonitrile, and then 1.62 g of 1-chloroethyl chlorocarbonate was added thereto, followed by heating under refluxing overnight. After the reaction solution was concentrated, 50 ml of methanol was added thereto, followed by heating under refluxing overnight. After the reaction solution was concentrated, water was added thereto, followed by washing with ether. The aqueous phase was made basic with a 1M sodium hydroxide aqueous solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then solvent was removed by evaporation to obtain 1.11 g of the title compound.

Workup

  1. temperatureby heating
  2. temperatureunder refluxing overnight
  3. concentrationAfter the reaction solution was concentrated
  4. addition50 ml of methanol was added
  5. temperatureby heating
  6. temperatureunder refluxing overnight
  7. concentrationAfter the reaction solution was concentrated
  8. additionwater was added
  9. washby washing with ether
  10. extractionfollowed by extraction with ethyl acetate
  11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  12. customsolvent was removed by evaporation

Sources & evidence

ORD record
ord-176f769011e24b82946e5000e3404398
Source dataset
uspto-grants-2007_11
Patent number
US07297698B2

Reaction notes

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