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

HRID 277991Notes

Reaction equation

HRID 277991 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=1>C(O)C.O1CCCC1.CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1

Participants

4

Reactant 1

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

Product 1

HCID 113795615-methoxy-3-(1-methylpiperidin-4-yl)-1H-indoleYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 66624091Ethanol tetrahydrofuran methanolSolvent

Procedure

5-Methoxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)indole (9.00 g, 37 mmol) was dissolved in 190 mL of ethanol/tetrahydrofuran/methanol (10:10:1). 10% palladium on carbon (2.2 g) was added, and the reaction mixture was hydrogenated at 40 p.s.i. in a Parr shaker for 96 hours. The mixture was filtered through celite, the catalyst was washed with ethanol, and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel (5-10% 2M ammonia-methanol/dichloromethane) to provide 8.79 g (97%) of the title compound. MS(m/e): 245 (M+). EA calculated for C14H19N3O: C, 68.54; H, 7.81; N, 17.13. Found: C, 68.40; H, 7.52; N, 16.90.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe catalyst was washed with ethanol
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on silica gel (5-10% 2M ammonia-methanol/dichloromethane)

Sources & evidence

ORD record
ord-51bbd5a46bc34511b3c13486cdf4eccd
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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