Dimethylformamide → 3-(4-[5,6-Dimethoxy-1,2-benzisoxazol-3-yl]piperidyl}-2-methyl indole

HRID 223265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 223265
[CH3:1][O:2][C:3]1[C:4]([O:18][CH3:19])=[CH:5][C:6]2[O:10][N:9]=[C:8]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:7]=2[CH:17]=1.[CH3:20][C:21]1[NH:22][C:23]2[C:28]([C:29]=1CCCS(C1C=CC=CC=1)(=O)=O)=[CH:27][CH:26]=[CH:25][CH:24]=2.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][O:2][C:3]1[C:4]([O:18][CH3:19])=[CH:5][C:6]2[O:10][N:9]=[C:8]([CH:11]3[CH2:12][CH2:13][N:14]([C:29]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[NH:22][C:21]=4[CH3:20])[CH2:15][CH2:16]3)[C:7]=2[CH:17]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 130764265,6-Dimethoxy-3-(4-piperidyl)-1,2-benzisoxazoleHCID 134509002-Methyl-3-(phenylsulfonylpropyl)indole

Produkt 1

HCID 867385873-(4-[5,6-Dimethoxy-1,2-benzisoxazol-3-yl]piperidyl}-2-methyl indoleAusbeute 26,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A stirred mixture of 5.0 g of 5,6-dimethoxy-3-(4-piperidyl)-1,2-benzisoxazole, 6.78 g of 2-methyl-3-(phenylsulfonylpropyl)indole, 120 ml of dimethylformamide and 15.0 g of anhydrous potassium carbonate was heated to 90° for 6 hrs and overnight at ambient temperature. The mixture was poured into water (300 ml) and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to yield a solid. The solid was purified by passing it through a silica gel column (20:1) and eluting it with dichloromethane-methanol (1%). Recrystallization two times from ethanol-water yielded 2.0 g (24%) of product, mp 176°-178°.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customto yield a solid
  5. customThe solid was purified
  6. washeluting it with dichloromethane-methanol (1%)
  7. customRecrystallization two times from ethanol-water

Quellen und Nachweise

ORD-Eintrag
ord-11c789af77164c3e95c1fe0087bc6bf8
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04352811

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