Water → HCID 13078392, compound

HRID 223257Notes

Reaction equation

HRID 223257 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:3][CH2:2]1.[CH3:17][C:18]1[NH:19][C:20]2[C:25]([C:26]=1[CH2:27][CH2:28][CH2:29]S(C1C=CC=CC=1)(=O)=O)=[CH:24][CH:23]=[CH:22][CH:21]=2.C(=O)([O-])[O-].[K+].[K+].O>C(C(C)=O)C>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]2[C:7]([CH:4]3[CH2:3][CH2:2][N:1]([CH2:29][CH2:28][CH2:27][C:26]4[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[NH:19][C:18]=4[CH3:17])[CH2:6][CH2:5]3)=[N:8][O:9][C:10]=2[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13076430HCID 13076430, compoundHCID 134509002-Methyl-3-(phenylsulfonylpropyl)indole

Product 1

HCID 13078392HCID 13078392, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred mixture, under nitrogen, of 27.0 g of 3-(4-piperidyl-6-chloro-1,2-benzisoxazole, 31.3 g of 2-methyl-3-(3-phenylsulfonylpropyl)indole and 27.6 g of anhydrous potassium carbonate in 500 ml of methyl ethyl ketone was heated under reflux for 6 hrs. The mixture was cooled and treated with 150 ml of water. The organic phase was separated, extracted with water and concentrated to an oily residue. The residue was dissolved in 50 ml of ethyl acetate and absorbed on a chromatography column containing 300 g of silica gel packed in ethyl acetate. Elution with ethyl acetate, followed by concentration of the eluent and trituration with ether, provided 12.1 g (31% yield) of product. Recrystallization from a small volume of toluene afforded the anlytical sample, mp 108°-110°.

Workup

  1. temperatureunder reflux for 6 hrs
  2. temperatureThe mixture was cooled
  3. customThe organic phase was separated
  4. extractionextracted with water
  5. concentrationconcentrated to an oily residue
  6. dissolutionThe residue was dissolved in 50 ml of ethyl acetate
  7. customabsorbed on a chromatography column
  8. additioncontaining 300 g of silica gel
  9. washElution with ethyl acetate

Sources & evidence

ORD record
ord-cdb2ef3b01f349e989ba197f2102a4a7
Source dataset
uspto-grants-1982_10
Patent number
US04352811

Reaction notes

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