Water → HCID 13490827, compound

HRID 2290205Notes

Reaction equation

HRID 2290205 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>C1(C)C=CC=CC=1.CN(C)C=O>[CH2:26]([N:17]1[CH2:18][CH2:19][CH:14]([NH:13][C:11]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]=2[CH3:1])=[O:12])[CH2:15][CH2:16]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 13752625HCID 13752625, compound

Product 1

HCID 13490827HCID 13490827, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1.2 g of 2-methyl-N-(4-piperidyl)indole-3-carboxamide and 1 g of potassium carbonate in 50 ml of toluene and 10 ml of dimethylformamide was added dropwise 0.6 g of benzyl chloride. The mixture was refluxed under heating for 3 hours. After cooling, 50 ml of water was poured into the mixture. The insoluble materials precipitated were filtered by suction and recrystallized from methanol to give N-(1-benzyl-4-piperidyl)-2-methylindole-3-carboxamide, melting at 150°-153° C.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 3 hours
  3. temperatureAfter cooling
  4. customThe insoluble materials precipitated
  5. filtrationwere filtered by suction
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-95b6a826e2294a069d3bc1d0ce0338cc
Source dataset
uspto-grants-1986_10
Patent number
US04616009

Reaction notes

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