1-Acetylnaphthalene → HCID 69200119, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-acetonaphthone (152 μl, 1 mmol) in acetonitrile (2 ml) was added tert-butyl N-(3-aminopropyl)-carbamate (209 μl, 1.2 mmol), NaBH3CN (126 mg, 2 mmol) and anhydrous ZnCl2 (136 mg, 1 mmol). The reaction was heated for 70 hours at 80° C. in a screw cap vial with magnetic stirring. The precipitate was filtered off and the solution was evaporated. The residue was dissolved in 3 ml 0.1N HCl and extracted with methylenchloride (1×5 ml). The organic layer was dried (Na2SO4) and evaporated. The crude product was purified by silica gel flash chromatography using 1. CHCl2/MeOH (10/0.1) and 2. CH2Cl2/MeOH (10/1), as an eluent, to give an oily product 70%. The structure characterization of the products was made with 1HNMR; 13CNMR; MS (m/z): 329 (MH+).

Provenance & Evidence