Butanal → N-[2-[3-(Butylamino)propyl]-6-chloro-5-quinolinyl]-cyclohexaneacetamide dihydrochloride

Participants

Reaction Conditions

Reaction Steps

A solution of N-[2-(3-aminopropyl)-6-chloro-5-quinolinyl]-cyclohexaneacetamide (0.2 g) (Example 23), acetic acid (1 drop) and butanal (0.074 mL) in tetrahydrofuran was placed in a 10 mL vial and heated at 100° C. for 30 minutes within a microwave. Once the reaction had cooled to room temperature sodium triacetoxyborohydride (0.236 g) was added and the mixture stirred for 12 hours. The solvent was removed and the residue taken up in dimethylsulfoxide (3 mL). The residue was purified by HPLC (Waters Symmetry column using 25% to 95% acetonitrile in 0.1% aqueous trifluoroacetic acid). Further purification (SiO2, ammonia:methanol:dichloromethane, 1:4:95 as eluant) followed by removal of solvent and conversion to its hydrochloride salt with 4M hydrogen chloride in 1,4-dioxane (5 mL) afforded the title product (0.021 g).

Provenance & Evidence