Pyridinium chloride → 7-Methyl-3-(1-methylpiperidin-4-yl)-1H-indole-5-ol

HRID 1766223Notes

Reaction equation

HRID 1766223 reaction equation
C[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[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.Cl.N1C=CC=CC=1>O>[CH3:12][C:10]1[CH:11]=[C:3]([OH:2])[CH:4]=[C:5]2[C:9]=1[NH:8][CH:7]=[C:6]2[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 179800985-methoxy-7-methyl-3-(1-methylpiperidin-4-yl)-1H-indole

Product 1

HCID 179800997-Methyl-3-(1-methylpiperidin-4-yl)-1H-indole-5-olYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a round bottom flask was placed 5-methoxy-7-methyl-3-(1-methylpiperidin-4-yl)-1H-indole (3.9 mmole, 1.01 g) and pyridine hydrochloride (25 g). The flask was then placed in a preheated oil bath set at 190° C. for 45 minutes. This solution was cooled to room temperature. The resulting solidified material was dissolved in water (200 mL). The pH was adjusted to approximately 10.3, which resulted in a precipitate. The insoluble material was collected by filtration, rinsed with water to afford 0.781 g (82%) of the title compound: mass spectrum (ion spray): m/z=245 (M+1); 1H NMR (DMSOd6): 10.40 (s, 1H), 8.45 (s, 1H), 6.93 (s, 1H), 6.68 (s, 1H), 6.40 (s, 1H), 2.90 (m, 2H), 2.60 (m, 1H), 2.36 (s, 3H), 2.26 (s, 3H), 2.08 (m, 2H), 1.90 (m, 2H), 1.70 (m, 2H); Calculated for C15H20N2O: C, 73.74; H, 8.25; N, 11.47. Found: C, 73.76; H, 8.15; N, 11.71.

Workup

  1. customIn a round bottom flask was placed
  2. customThe flask was then placed in a preheated oil bath
  3. customresulted in a precipitate
  4. filtrationThe insoluble material was collected by filtration
  5. washrinsed with water

Sources & evidence

ORD record
ord-3a3c83c94be84893a55c5969603f2dea
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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