Dimethylamine → 8,9-dihydro-10-[(dimethylamino)methyl]-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one

HRID 1681745Notes

Reaction equation

[CH3:1][NH:2][CH3:3].[CH2:4]=O.[CH3:6][C:7]1[NH:11][CH:10]=[N:9][C:8]=1[CH2:12][CH:13]1[C:25](=[O:26])[N:17]2[C:18]3[C:23]([CH:24]=[C:16]2[CH2:15][CH2:14]1)=[CH:22][CH:21]=[CH:20][CH:19]=3>C(O)(=O)C>[CH3:1][N:2]([CH2:4][C:24]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]2[C:25](=[O:26])[CH:13]([CH2:12][C:8]3[N:9]=[CH:10][NH:11][C:7]=3[CH3:6])[CH2:14][CH2:15][C:16]=12)[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of aqueous 50% dimethylamine solution (0.20 ml), aqueous 35% formaldehyde solution (0.20 ml), and acetic acid (4 ml) at 15° C. was added 8,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (418 mg). The mixture was heated at 60° C. for 24 hours. After evaporation of the solvent, the residue was dissolved in water, made basic with aqueous 3N sodium hydroxide solution, and extracted three times with chloroform. The chloroform layer was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The oil was purified by silica gel column chromatography (20% methanol-chloroform) to give 8,9-dihydro-10-[(dimethylamino)methyl]-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (240 mg).

Workup

customAfter evaporation of the solvent
dissolutionthe residue was dissolved in water
extractionextracted three times with chloroform
washThe chloroform layer was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
customevaporated in vacuo
customThe oil was purified by silica gel column chromatography (20% methanol-chloroform)

Sources & evidence

ORD record: ord-bcb368ceaf604973843a4fc7282e9e1c
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05173493

Reaction notes

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