Cyclohexanemethylamine → N-1H-Indol-4-ylbenzamide

HRID 414200Notes

Reaction equation

HRID 414200 reaction equation
O1CC1CO[C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2)=[O:9].C1(CN)CCCCC1>C(O)C>[NH:15]1[C:16]2[C:12](=[C:11]([NH:10][C:8](=[O:9])[C:7]3[CH:6]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

Participants

4

Reactant 2

HCID 76688CyclohexanemethylamineHCID 15611138HCID 15611138, compound

Product 1

HCID 4614391N-1H-Indol-4-ylbenzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.5 g of 2-[(2-oxiranyl)methoxy]-N-(1H-indol-4-yl)-benzamide in 50 ml of ethanol in the presence of 1.147 g of cyclohexane methylamine was refluxed for 2 hours and 15 minutes and the solvent was evaporated under reduced pressure. The residue was chromatographed over silica (eluent: methylene chloride--methanol, 9-1) to obtain 1.97 g of 2-[3-(cyclohexylmethyl)amino]-2-hydroxypropoxy]-N-(1H-indol-4-yl)-benzamide.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was chromatographed over silica (eluent: methylene chloride--methanol, 9-1)

Sources & evidence

ORD record
ord-1d97c53dfa124db2b95901fcf874db39
Source dataset
uspto-grants-1988_12
Patent number
US04791109

Reaction notes

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