Indole → 1-(4-benzoyl-1-piperidyl)-2-(1H-indol-3-yl)ethane-1,2-dione

HRID 866996

Reaction equation

HRID 866996 reaction equation
N1C2C(=CC=CC=2)C=C1.C(Cl)(=O)C(Cl)=O.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:25](=[O:29])[C:26](Cl)=[O:27])=[CH:17]1.[C:30]([CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.CCOCC>[C:30]([CH:38]1[CH2:43][CH2:42][N:41]([C:26](=[O:27])[C:25]([C:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:16][CH:17]=2)=[O:29])[CH2:40][CH2:39]1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 798IndoleHCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 899523-Indoleglyoxylyl chlorideHCID 226102Phenyl(piperidin-4-yl)methanone

Product 1

HCID 203117111-(4-benzoyl-1-piperidyl)-2-(1H-indol-3-yl)ethane-1,2-dione

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

A sample of an indole of the formula ##STR7## in a solvent such as anhydrous ether is allowed to react with oxalyl chloride at a temperature of from -15° to 15° C. for from a couple of minutes to one hour to produce a mixture of a corresponding 3-indoleglyoxyloyl chloride in the solvent which is then added to a cooled solution of 4-benzoylpiperidine in a suitable organic solvent such as chloroform optionally containing an acid scavenger such as potassium carbonate and allowing the mixture to react at a temperature of from 15° to 40° C. for a few minutes to 12 hours to produce a 4-benzoyl-1-(indol-3-ylglyoxyloyl)piperidine of the formula ##STR8##

Workup

  1. customto produce
  2. customto react at a temperature of from 15° to 40° C. for a few minutes to 12 hours

Sources & evidence

ORD record
ord-dc7ca59438ab48e38566a4526c4c79c1
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Linked notes

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