Acetic Acid → HCID 19824917, compound

HRID 727773Notes

Reaction equation

HRID 727773 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.[C:21]1([CH2:27][N:28]2[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[NH4+].[OH-]>CCO>[C:21]1([CH2:27][N:28]2[CH2:33][CH2:32][C:31]3([C:16]4=[C:15]5[C:10](=[N:9][C:8]4=[C:3]4[C:2](=[CH:7][CH:6]=[CH:5][CH2:4]4)[NH:1]3)[CH:11]=[CH:12][CH:13]=[CH:14]5)[CH2:30][CH2:29]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 19824917HCID 19824917, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture prepared from 7.6 g of 2-(2-aminophenyl)indole, 2.5 ml of acetic acid and 90 ml of ethanol was added 7.4 ml of 1-phenylmethyl-4-piperidone. The resultant solution was refluxed for 6 hours. Concentration gave a solid/gum mixture which was taken up in EtOH and treated with dilute NH4OH. Filtration gave 12.45 g of yellow solid. This was recrystallized from CH3OH/H2O to give 9.0 g of yellow solid. High vacuum drying (90°) gave 2.6 g of dark yellow solid, m.p. 155°-157° C.

Workup

  1. concentrationConcentration
  2. customgave a solid/gum mixture which
  3. filtrationFiltration

Sources & evidence

ORD record
ord-2803d0663b594dae9b1db4efa0c2a8ae
Source dataset
uspto-grants-1991_09
Patent number
US05045539

Reaction notes

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