Ammonium Hydroxide → HCID 15233281, compound

HRID 343903Notes

Reaction equation

HRID 343903 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[N+:9]([CH2:12][CH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[CH:17]2)([O-:11])=[O:10].[NH4+].[OH-]>C(O)(=O)C>[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:17]2[C:16]3[C:20](=[CH:21][CH:22]=[C:14]([CH2:13][CH2:12][N+:9]([O-:11])=[O:10])[CH:15]=3)[NH:19][CH:18]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 740491-Methyl-4-piperidoneHCID 131097235-(2-nitroethyl)-1H-indole

Product 1

HCID 15233281HCID 15233281, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

N-Methyl-4-piperidone (Aldrich, 4.2 g) was added to a solution of the product from step (c) (2.3 g) in glac. acetic acid (35 ml) at 100° C. The resulting solution was heated at 100° C. for 1 hour, cooled and poured into a mixture of 0.88 NH4OH (61 ml) and ice (61 g). The resulting solid was filtered off, dried and recrystallised from ethanol to give the desired product as a white solid (1.6 g).

Workup

  1. customat 100° C
  2. temperaturecooled
  3. filtrationThe resulting solid was filtered off
  4. customdried
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-647e3adc46dd4deb96ce808a45ee200f
Source dataset
uspto-grants-1999_01
Patent number
US05863935

Reaction notes

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