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

HRID 277990Notes

Reaction equation

HRID 277990 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

5

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidoneHCID 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.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux temperature overnight
  3. customThe resulting precipitate was collected
  4. concentrationthe filtrate was concentrated to a minimal volume
  5. customA second crop of crystals was collected
  6. washwashed with cold methanol

Sources & evidence

ORD record
ord-20b43238890945cea83ead14183523c4
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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