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

HRID 437576노트

반응식

HRID 437576 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 6212Chloroform용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b4dbe3f9b35043009e4f5f02c5b024c1
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04031221

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