Ammonia → 7-Chloro-1-(cyclohexylmethyl)-1H-indole-3-carboxamide

HRID 2358458Notes

Reaction equation

HRID 2358458 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[N:15]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH:14]=[C:13]2[C:24]([OH:26])=O.[NH3:27].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[N:15]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH:14]=[C:13]2[C:24]([NH2:27])=[O:26]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 686740091-cyclohexylmethyl-7-chloro-1H-indole-3-carboxylic acid

Product 1

HCID 686750957-Chloro-1-(cyclohexylmethyl)-1H-indole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (4.95 g, 39.0 mmol) was added dropwise to a mixture of 7-chloro-1-(cyclohexyl)methyl-1H-indole-3-carboxylic acid (6.4 g, 21.9 mmol) and dichloromethane (150 ml) under ice-water cooling and the resulting mixture was stirred at room temperate for 20 h. Dichloromethane and excess oxalyl chloride were removed by evaporation and the obtained residue was mixed with dichloromethane (100 ml). Aqueous ammonia (33%, 50 ml) and potassium carbonate (6.05 g, 43.8 mmol) was added into the mixture under ice-water bath cooling. After stirring at room temperature for 2 h, the reaction mixture was concentrated in vacuo, then the obtained solid was washed with water, then n-heptane, and dried under reduced pressure to afford 7-chloro-1-(cyclohexyl)methyl-1H-indole-3-carboxylic acid amide (6.4 g, 22.0 mmol).

Workup

  1. customDichloromethane and excess oxalyl chloride were removed by evaporation
  2. additionthe obtained residue was mixed with dichloromethane (100 ml)
  3. temperaturecooling
  4. stirringAfter stirring at room temperature for 2 h
  5. concentrationthe reaction mixture was concentrated in vacuo
  6. washthe obtained solid was washed with water
  7. dry with materialn-heptane, and dried under reduced pressure

Sources & evidence

ORD record
ord-d3d88f9275d34e9f83923c752baed0ed
Source dataset
uspto-grants-2010_07
Patent number
US07763732B2

Reaction notes

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