Potassium Hydroxide → HCID 59259341, compound

HRID 641882Notes

Reaction equation

HRID 641882 reaction equation
[N:1]1([C:6]2[CH:14]=[C:13]3[C:9]([CH:10]=[CH:11][NH:12]3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].[CH3:17][N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1>CO>[CH3:17][N:18]1[CH2:19][CH:20]=[C:21]([C:10]2[C:9]3[C:13](=[CH:14][C:6]([N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:7][CH:8]=3)[NH:12][CH:11]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 21709049HCID 21709049, compound

Product 1

HCID 59259341HCID 59259341, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
72 °C

Procedure

6-(pyrrolidin-1-yl)-1H-indole (500 mg, 2.68 mmol) was added to a solution of potassium hydroxide (1.55 g, 27.62 mmol) in methanol (20 mL). 1-methylpiperidin-4-one (610 mg, 5.39 mmol) was then added, and the resulting solution was stirred at 72° C. overnight. The mixture was concentrated and the residue was poured into water (40 mL). After filtration, the filter cake was washed with water (1×50 mL) and diethylether (1×50 mL), to afford 400 mg (47.6%) of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-6-(pyrrolidin-1-yl)-1H-indole as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was poured into water (40 mL)
  3. filtrationAfter filtration
  4. washthe filter cake was washed with water (1×50 mL) and diethylether (1×50 mL)

Sources & evidence

ORD record
ord-be69a723fa8b44dca48ac510e0d248d0
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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