Piperidine → 2-[3-(4-Chlorophenyl)-1,2-dimethyl-1H-indole-5-yloxy]-2-methyl-propanoic acid piperidide

HRID 66911Notes

Reaction equation

HRID 66911 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]([CH3:23])([CH3:22])[C:19]([OH:21])=O)[CH:15]=3)[N:10]([CH3:24])[C:9]=2[CH3:25])=[CH:4][CH:3]=1.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]([CH3:23])([CH3:22])[C:19]([N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[O:21])[CH:15]=3)[N:10]([CH3:24])[C:9]=2[CH3:25])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 3059432Propanoic acid, 2-((3-(4-chlorophenyl)-1,2-dimethyl-1H-indol-5-yl)oxy)-2-methyl-

Product 1

HCID 544814402-[3-(4-Chlorophenyl)-1,2-dimethyl-1H-indole-5-yloxy]-2-methyl-propanoic acid piperidide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An amount of 0.5 g (1.4 m mole) of 2-[3-(4-chlorophenyl)-1,2-dimethyl-1H-indole-5yloxy]-2-methyl-propanoic acid was dissolved in 25 ml of tetrahydrofurane and heated for four hours with 0.24 g (1.4 m mole) of N,N'-carbonyldiimidazole on a steam bath. Subsequently, 0.24 g (2.8 m mole) of piperidine were added, and the mixture was refluxed for 12 hours. After evaporation the residue was mixed with dilute hydrochloric acid and extracted with ether. The evaporated ether residue was purified by column chromatography with toluene/ethyl acetate (8:2) on silicagel.

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. customAfter evaporation the residue
  3. additionwas mixed with dilute hydrochloric acid
  4. extractionextracted with ether
  5. customThe evaporated ether residue was purified by column chromatography with toluene/ethyl acetate (8:2) on silicagel

Sources & evidence

ORD record
ord-69e55098d6d7410181e34fa016e6602f
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Reaction notes

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