Acetic Acid → HCID 19824934, compound

HRID 727770Notes

Reaction equation

HRID 727770 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.C(O)(=O)C.[CH3:21][N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1>C(O)C>[CH3:21][N:22]1[CH2:27][CH2:26][C:25]2([C:16]3=[C:15]4[C:10](=[N:9][C:8]3=[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH2:4]3)[NH:1]2)[CH:11]=[CH:12][CH:13]=[CH:14]4)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 740491-Methyl-4-piperidoneHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 19824934HCID 19824934, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution prepared from 8 g of 2-(2-aminophenyl)indole, 2.5 ml of acetic acid and 100 ml of ethanol was added 5.15 g of 1-methyl-4-piperidone. The mixture was refluxed for 6 hours. Concentration gave a gum which was triturated with dilute NH4OH and the resultant solid was collected. Flash chromatography using 10% CH3OH/CH2Cl2 as an eluent gave 4.15 g of yellow solid, m.p. 228°-230° dec.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. concentrationConcentration
  3. customgave a gum which
  4. customwas triturated with dilute NH4OH
  5. customthe resultant solid was collected

Sources & evidence

ORD record
ord-83bd0af77b844f07898944b5d7105241
Source dataset
uspto-grants-1991_09
Patent number
US05045539

Reaction notes

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