Methanol → 1-[(5-Chloroisoindol-2-yl)sulfonyl]piperazine

HRID 352779Notes

Reaction equation

HRID 352779 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([S:14]([N:17]2[CH:25]=[C:24]3[C:19]([CH:20]=[CH:21][C:22]([Cl:26])=[CH:23]3)=[CH:18]2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.CO>ClCCCl>[Cl:26][C:22]1[CH:21]=[CH:20][C:19]2[C:24](=[CH:25][N:17]([S:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)(=[O:16])=[O:15])[CH:18]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 227101621-Benzyl-4-[(5-chloroisoindol-2-yl)sulfonyl]piperazine

Product 1

HCID 227095061-[(5-Chloroisoindol-2-yl)sulfonyl]piperazine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-benzyl-4-[(5-chloroisoindol-2-yl)sulfonyl]piperazine (222 mg) in 1,2-dichloroethane (20 ml), 1-chloroethyl chloroformate (81 mg) was added under ice cooling. The resulting mixture was stirred for 15 minutes and then heated under reflux for 1 hour. After cooling, anhydrous methanol was added to the residue obtained by distilling off the solvent under reduced pressure. The mixture was heated under reflux for 11 hours. After cooling, the residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (ethanol:dichloromethane=1:50 to 1:10), whereby the title compound (120 mg, 70%) was obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. customobtained
  5. distillationby distilling off the solvent under reduced pressure
  6. temperatureThe mixture was heated
  7. temperatureunder reflux for 11 hours
  8. temperatureAfter cooling
  9. customthe residue obtained
  10. distillationby distilling off the solvent under reduced pressure
  11. customwas purified by chromatography on a silica gel column (ethanol:dichloromethane=1:50 to 1:10), whereby the title compound (120 mg, 70%)
  12. customwas obtained

Sources & evidence

ORD record
ord-f8520d48894a40f2a0e2d7c70c27bcaf
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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