8-Methylimidazo(1,2-a)pyridine → 8-Methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine
Reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([CH:8]=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1>C(O)CCC.[Ni]>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]2[CH:8]=[CH:9][N:10]=[C:3]12Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
1 g of 8-methylimidazo[1,2-a]pyridine [3-1] was dissolved in 20 mL of 1-butanol, and a catalytic amount of Raney nickel of was added thereto. The mixture was stirred under a hydrogen atmosphere (5 atmospheric pressure) at 65° C. for 4 days. After cooling the reaction mixture back to room temperature, the insolubles were filtered through celite, and washed with methanol. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, to obtain 823.3 mg of 8-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine [46-1].
Workup
- temperatureAfter cooling the reaction mixture back to room temperature
- filtrationthe insolubles were filtered through celite
- washwashed with methanol
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-8f3eeb8f5b18457c8a4ed2edf6b5570b
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718801B2
Reaction notes
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