Potassium Carbonate → 1-(5,6-Dimethoxy-2-methylindol-3-ylglyoxyloyl)-4-(p-trifluoromethylphenoxy)piperidine

HRID 437576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 437576
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][C:13]([CH3:20])=[CH:12]2.[F:21][C:22]([F:37])([F:36])[C:23]1[CH:35]=[CH:34][C:26]([O:27][CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(Cl)(Cl)Cl.CCOCC>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][C:13]([CH3:20])=[C:12]2[C:1](=[O:5])[C:2]([N:31]1[CH2:30][CH2:29][CH:28]([O:27][C:26]2[CH:25]=[CH:24][C:23]([C:22]([F:21])([F:36])[F:37])=[CH:35][CH:34]=2)[CH2:33][CH2:32]1)=[O:3]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 2665965,6-dimethoxy-2-methyl-1H-indoleHCID 36883924-(4-(Trifluoromethyl)phenoxy)piperidine

Produkt 1

HCID 214287111-(5,6-Dimethoxy-2-methylindol-3-ylglyoxyloyl)-4-(p-trifluoromethylphenoxy)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

6.5 g of oxalyl chloride are added dropwise to a stirred solution of 8.8 g of 5,6-dimethoxy-2-methylindole in 160 ml. of ether at -10° C. After addition is complete, the mixture is stirred for 10 minutes and a bright orange precipitate of 5,6-dimethoxy-2-methyl-indole-3-glyoxyloyl chloride appears. The ether suspension of 5,6-dimethoxy-2-methyl-indole-3-glyoxyloyl chloride is added portion wise to a cooled stirring mixture of 12.3 g of 4-(p-trifluoromethylphenoxy)piperidine, 12.5 g of potassium carbonate, 50 ml. of chloroform and 60 ml. of water. The reaction mixture is stirred overnight and the resultant white solid is collected and dried. The solid is recrystallized twice from a methanol and water mixture to give 1-(5,6-dimethoxy-2-methylindol-3-ylglyoxyloyl)-4-(p-trifluoromethylphenoxy)piperidine m.p. 211°-213° C.

Aufarbeitung

  1. customat -10° C
  2. additionAfter addition
  3. additionis added portion wise to a cooled
  4. stirringstirring
  5. stirringThe reaction mixture is stirred overnight
  6. customthe resultant white solid is collected
  7. customdried
  8. customThe solid is recrystallized twice from a methanol and water mixture

Quellen und Nachweise

ORD-Eintrag
ord-b4dbe3f9b35043009e4f5f02c5b024c1
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04031221

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