Potassium Hydroxide → 5-Methoxy-7-methyl-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 1766221Notes

Reaction equation

HRID 1766221 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]=[CH:6]2.[OH-].[K+].[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]=[C:6]2[C:19]1[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH:18]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 123389175-Methoxy-7-methyl-1H-indole

Product 1

HCID 179800975-Methoxy-7-methyl-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By a method similar to Preparation 3, using 5-methoxy-7-methyl-1H-indole (0.12 mole, 20.02 g), methanol (240 mL), potassium hydroxide (0.43 mole, 24.39 g) and 1-methyl-4-piperidone (0.13 mole, 14.76 g) afforded 24.72 (78%) of the title compound: Mass spectrum (ion spray): m/z=(ES+) 257 (M+1), (ES−) 255 (M−1); 1H NMR (DMSOd6): 7.32 (s, 1H), 7.06 (1H), 6.59 (1H), 6.05 (m, 1H), 3.75 (s, 3H), 3.04 (2H), 2.50 (m, 4H), 2.42 (s, 3H), 2.29 (s, 3H).

Workup

  1. customBy a method similar to Preparation 3

Sources & evidence

ORD record
ord-c77abe517e114126907fc38eb1c3dac1
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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