Acetic Acid → HCID 19824931, compound

HRID 1084719Notes

Reaction equation

HRID 1084719 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.[NH:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1.O.Cl.[NH4+].[OH-]>C(O)C>[NH:21]1[CH2:26][CH2:25][C:24]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)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 7359662-(2-Aminophenyl)indoleHCID 2723901Piperonylamine

Product 1

HCID 19824931HCID 19824931, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture prepared from 8 g of 2-(2-aminophenyl)indole, 2.5 ml of acetic acid and 100 ml of ethanol was added 6.5 g of 4-piperidone·H2O·HCl. The mixture was refluxed for 6 hours and thereafter cooled to room temperature. The resultant mixture was treated with dilute NH4OH and the resultant solid was collected, washed with water and dried. The crude product (9.15 g) was flash chromatographed using CH3OH as an eluent, and thereafter converted to the HCl salt. This salt was converted back to the free base using CH2Cl2 /dilute NH4OH to give 5.96 g of solid, m.p. 257°-259° dec.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customthe resultant solid was collected
  3. washwashed with water
  4. customdried
  5. customchromatographed

Sources & evidence

ORD record
ord-38a04c50a9dd45f3b14cc05996632e6b
Source dataset
uspto-grants-1991_04
Patent number
US05006531

Reaction notes

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