Ammonium Hydroxide → HCID 19824931, compound

HRID 727769Notes

Reaction equation

HRID 727769 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.[NH:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.O.Cl.[NH4+].[OH-]>C(O)C.C(O)(=O)C>[NH:17]1[CH2:22][CH2:21][C:20]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)[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 337214-PiperidoneHCID 7359662-(2-Aminophenyl)indoleHCID 21885828Hydrate;hydrochloride

Product 1

HCID 19824931HCID 19824931, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 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-f71d7b18440e407488a06e47edb76310
Source dataset
uspto-grants-1991_09
Patent number
US05045539

Reaction notes

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