Ethanol → 8-Benzyloxy-3-dimethylaminoethyl-2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Reaction equation

[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]2[CH:15]=[C:16]([CH3:18])[N:17]=[C:10]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:20][NH:21][CH3:22].C=O.[CH2:25](O)[CH3:26]>>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([CH2:26][CH2:25][N:21]([CH3:22])[CH3:20])=[C:16]([CH3:18])[N:17]=[C:10]12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 4

HCID 702Ethanol

HCID 712Formaldehyde

HCID 10473Dimethylamine, hydrochloride

HCID 139003398-Benzyloxy-2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Product 1

HCID 544310968-Benzyloxy-3-dimethylaminoethyl-2-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

Procedure

A mixture consisting of the product of Example 20 (1.52 g), dimethylamine hydrochloride (565 mg), paraformaldehyde (238 mg) and ethanol (10 ml) was refluxed for four hrs. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue was dissolved in chloroform, the solution washed four times with 5% aqueous potassium carbonate, dried over Na2SO4 and then the solvent was evaporated on a rotary evaporator. The residue was chromatographed on silica gel, eluting with acetone, to obtain the title compound (m.p. 68°-70° C.).