5-Tetralinylamine → HCID 178419826, compound

Participants

Reaction Conditions

Reaction Steps

5,6,7,8-Tetrahydro-1-naphthylamine (Aldrich, 159 mg, 1.06 mmol), imidazoline-2-sulfonic acid (147.0 mg, 1.0 mmol, Compound 7 obtained as described above) and CH3CN (5ml) were placed in a thick-walled cap which was sealed with a TEFLON™ screw and heated to 155° C. for 1.25 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in CHCl3 and washed with aq. 1N NaOH (to pH 13). The organic layer was separated, washed with brine, dried over Na2CO3 and concentrated in vacuo to yield a brown oil. The crude material was purified by flash chromatography (SiO2 ; 80:20 CHCl3 /CH3OH saturated with NH3) to yield 29.5 mg (14%) of the title compound as a white solid: mp 138°-141° C.; 1H NMR (300 MHz, CDCl3) & 7.05 (t, 1H) 6.82 (m, 2 H); 5.41 (br, 2H); 3.50 (s, 4H); 2.79 (m, 2H); 2.62 (m, 2H); 1.80 (m, 4H); Mass spectrum m/e 214.1339 (C13H16N3 requires 214.1344). Alternatively and preferably alcohols, most preferably isobutanol, are used instead of CH3CN in this reaction.

Provenance & Evidence