Methyl Ethyl Ketone → 3-[4-(5-Methoxy-1,2-benzisoxazole-3-yl)piperidyl]propyl-2-methylindole hydrochloride

HRID 223258Notes

Reaction equation

HRID 223258 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13]S(C1C=CC=CC=1)(=O)=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.[ClH:23].[CH3:24][O:25][C:26]1[CH:27]=[CH:28][C:29]2[O:33][N:32]=[C:31]([CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[C:30]=2[CH:40]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[ClH:23].[CH3:24][O:25][C:26]1[CH:27]=[CH:28][C:29]2[O:33][N:32]=[C:31]([CH:34]3[CH2:39][CH2:38][N:37]([CH2:13][CH2:12][CH2:11][C:10]4[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[NH:3][C:2]=4[CH3:1])[CH2:36][CH2:35]3)[C:30]=2[CH:40]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 130764254-(5-Methoxy-1,2-benzisoxazolyl)piperidine hydrochlorideHCID 134509002-Methyl-3-(phenylsulfonylpropyl)indole

Product 1

HCID 130783943-[4-(5-Methoxy-1,2-benzisoxazole-3-yl)piperidyl]propyl-2-methylindole hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.0 g of 2-methyl-3-(3-phenylsulfonylpropyl)indole, 3.0 g of 5-methoxy-3-(4-piperidyl)-1,2-benzisoxazole hydrochloride, 8.0 g of potassium carbonate and 70 ml of 2-butanone was heated under reflux, with stirring, and refluxed under nitrogen for 16 hours. The reaction mixture was poured into water and the aqueous suspension was extracted with ethyl acetate. The insoluble material was collected and washed with diluted sodium hydroxide to give a solid. The ethylacetate extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to give an additional solid. Treatment of the combined solids with a saturated hydrogen chloride-toluene solution gave the salt. The salt was triturated with acetone and recrystallized from ethanol-ether to give an ethanolate, mp 163°-165° (foaming). Recrystallization of the alcoholate from acetonitrile and subsequent drying of the sample at 100° and ca 1 mm gave 1.60 g (33%) of product, mp 130°-132°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperaturerefluxed under nitrogen for 16 hours
  4. extractionthe aqueous suspension was extracted with ethyl acetate
  5. customThe insoluble material was collected
  6. washwashed with diluted sodium hydroxide
  7. customto give a solid
  8. extractionThe ethylacetate extract
  9. washwas washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was removed in vacuo
  12. customto give an additional solid

Sources & evidence

ORD record
ord-08ac2bd6f4014cd6bc85708d5a553870
Source dataset
uspto-grants-1982_10
Patent number
US04352811

Reaction notes

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