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

Reaction equation

[CH3:1][O:2][C:3]1N=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[OH-].[K+].[CH3:14][N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.[CH3:22]O>>[CH3:1][O:2][C:3]1[CH:22]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:18]1[CH2:17][CH2:16][N:15]([CH3:14])[CH2:20][CH:19]=1

Participants

Reactant 4

HCID 887Methanol

HCID 14797Potassium Hydroxide

HCID 740491-Methyl-4-piperidone

HCID 53243695-methoxy-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 30552495-Methoxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleYield 79%

Procedure

To a mixture of 5-methoxy-4-aza-1H-indole(7.0 g, 47 mmol) and potassium hydroxide (9.2 g, 165 mmol) in 350 mL of methanol was added 1-methyl-4-piperidone (9.86 mL, 80 mmol) in one portion. The reaction was heated at reflux temperature overnight, and cooled to room temperature. The resulting precipitate was collected, and the filtrate was concentrated to a minimal volume. A second crop of crystals was collected, washed with cold methanol, and combined with the previous crop to afford 9.0 g (79%) of the title compound. MS(m/e): 243 (M+). EA calculated for C14H17N3O: C, 69.11; H, 7.04; N, 17.27. Found: C, 69.22; H, 7.13; N, 17.47.