1-Naphthalenemethanamine → HCID 57495446, compound

Participants

Reaction Steps

To a solution of suberic acid monomethyl ester 6c (376 mg, 2.0 mmol) in anhydrous tetrahydrofuran (5 ml) under argon atmosphere triethylamine (0.36 ml, 2.6 mmol) was added and the resulting solution was cooled in ice bath. To the mixture iso-butylchloroformate (0.3 ml, 2.3 mmol) was added and the reaction was stirred for 20 min, then a solution of 1-naphthylmethylamine 1/89 (314 mg, 2 mmol) in tetrahydrofuran (1.5 ml) was added. The mixture was stirred at ice bath temperature for 15 min and for 1 h at room temperature, diluted with brine (50 ml) and extracted with ethyl acetate (3×25 ml). The organic phase was washed with brine, 5% NaHCO3, brine, saturated KH2PO4, and brine. The organic layer was dried (Na2SO4) and the solvent was evaporated. The residue was purified on silica gel (20 g) with chloroform-ethyl acetate as eluent to give the title compound 7/89, yield 85.4%. 1H NMR (CDCl3, HMDSO) δ: 1.12-1.81(m, 8H); 2.16(t, J=8.0 Hz, 2H); 2.25(t, J=8.0 Hz, 2H); 3.63(s, 3H); 4.87(d, J=6.0 Hz, 2H); 5.61(br s, 1H); 7.32-7.63(m, 4H); 7.67-8.09(m, 3H).

Provenance & Evidence