3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole → 3-(4-Piperidinyl)-1H-indole

HRID 1766214Notes

Reaction equation

HRID 1766214 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1>[Pd].[Pt]=O>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 7022353-(4-Piperidinyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 82844Platinum oxide (PtO)Catalyst

Procedure

For example, a 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole of formula (3) may be hydrogenated over a catalyst, such as palladium on carbon or platinum oxide, to give a 3-(piperidin-4-yl)-1H-indole of formula (4). Such hydrogenations are generally carried out in a solvent and a variety of solvents are suitable, for example methanol, ethanol, or isopropanol, tetrahydrofuran, or mixed solvents, such as tetrahydrofuran and ethyl acetate. The hydrogenation may be performed at an initial hydrogen pressure of 20-180 psi (137-1241 kPa), preferably from 50-60 psi (345-413 kPa). The reaction is typically carried out at temperature of about 0° C. to about 60° C., preferably at temperatures of about 40° C. to 60° C. The reaction typically requires 1 hour to 3 days. The product can be isolated and purified by techniques well known in the art, such as filtration, extraction, evaporation, trituration, precipitation, chromatography, and recrystallization.

Sources & evidence

ORD record
ord-aa9cfa7766a84a479f527a8df342934e
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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