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

HRID 437576Notes

Reaction equation

HRID 437576 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6212ChloroformSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b4dbe3f9b35043009e4f5f02c5b024c1
Source dataset
uspto-grants-1977_06
Patent number
US04031221

Reaction notes

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