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

반응식

[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

참가 물질

반응물 4

HCID 887Methanol

HCID 14797Potassium Hydroxide

HCID 740491-Methyl-4-piperidone

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

생성물 1

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

실험 절차

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.