Hydrochloric Acid → HCID 10334592, compound

HRID 1681738Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:11](=[O:19])[CH:12]([CH2:15]N(C)C)[CH2:13][CH2:14][C:3]=12.[CH3:20][C:21]1[NH:22][CH:23]=[CH:24][N:25]=1.Cl.C(O)(C)C>C(Cl)Cl>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:11](=[O:19])[CH:12]([CH2:15][N:22]3[CH:23]=[CH:24][N:25]=[C:21]3[CH3:20])[CH2:13][CH2:14][C:3]=12

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 8,9-dihydro-10-methyl-7-(dimethylaminomethyl)pyrido[1,2-a]indol-6(7H)-one (0.65 g), 2-methylimidazole (0.76 g), 2N hydrochloric acid (1.27 ml), and isopropyl alcohol (4 ml) was heated at 100° C. for 3 hours and 15 minutes. After evaporation of the solvent, the residue obtained was dissolved in methylene chloride. The methylene chloride solution was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. Purification with neutral alumina column chromatography (0.5% methanol-methylene chloride), followed by recrystallization with ethyl acetate-hexane, gave 8,9-dihydro-10-methyl-7-[(2-methyl-1H-imidazol-1-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (0.40 g).

Workup

customAfter evaporation of the solvent
customthe residue obtained
washThe methylene chloride solution was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated in vacuo
customPurification with neutral alumina column chromatography (0.5% methanol-methylene chloride)
customfollowed by recrystallization with ethyl acetate-hexane

Sources & evidence

ORD record: ord-2be90c7b84154b7699617b02ac35e9e5
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05173493

Reaction notes

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