Aluminum(III) Chloride → 7-Hydroxy-4-methyl-6-(1-piperidinesulfonyl)-1-indanone

HRID 414685Notes

Reaction equation

HRID 414685 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]2[C:10]=1[C:9](=[O:11])[CH2:8][CH2:7]2.[N:13]1([S:19](Cl)(=[O:21])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[OH:1][C:2]1[C:3]([S:19]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:21])=[O:20])=[CH:4][C:5]([CH3:12])=[C:6]2[C:10]=1[C:9](=[O:11])[CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 11298344Piperidine-1-sulfonyl chlorideHCID 124362447-Hydroxy-4-methyl-1-indanone

Product 1

HCID 136041567-Hydroxy-4-methyl-6-(1-piperidinesulfonyl)-1-indanoneYield 32.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Into a solution of 2 g of 7-hydroxy-4-methyl-1-indanone in 10 ml of dichloroethane was added 2.27 g of 1-piperidine sulfonyl chloride. Then 10 g of anhydrous aluminum chloride was gradually added to the mixture and stirred, and the reaction mixture was refluxed by heating for 8 hours. The reaction mixture was extracted with 200 ml of chloroform, washed with water, then the chloroform was removed by evaporation under a reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent: chloroform), and recrystallized from ethanol to obtain 1.24 g of 7-hydroxy-4-methyl-6-(1-piperidinesulfonyl)-1-indanone.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. temperatureby heating for 8 hours
  3. extractionThe reaction mixture was extracted with 200 ml of chloroform
  4. washwashed with water
  5. customthe chloroform was removed by evaporation under a reduced pressure
  6. customThe residue was purified by means of a silica gel column chromatography (eluent: chloroform)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-44f3a295932047cc86a976dc939984c6
Source dataset
uspto-grants-1988_12
Patent number
US04792628

Reaction notes

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