4-[1-(Naphthalene-2-carbonyl)-piperidin-4-ylamino]benzoic acid tert-butyl ester → 4-[1-(Naphthalene-2-carbonyl)piperidin-4-ylamino]benzoic acid

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Reaction Conditions

Reaction Steps

A solution of (10) (0.039 g, 0.09 mmol) in HCl (5 mL, 4M in 1,4-dioxane) was capped with a drying tube and stirred at 25° C. for 12 h. The reaction mixture was concentrated to give a white solid residue (0.02 g, 57%); 1H NMR (DMSO) δ 7.98 (m, 4H), 7.66 (d, 2H, J=8.7), 7.55 (m, 3H), 6.65 (d, 2H, J=8.8), 4.41 (m, 2H), 3.67 (m, 1H), 3.15 (m, 2H), 1.95 (m, 2H), 1.40 (m, 2H); 13C NMR (DMSO) δ 169.0, 167.4, 151.1, 133.6, 133.1, 132.3, 131.1, 128.3, 128.1, 127.7, 127.1, 126.8, 126.1, 124.3, 117.3, 111.6, 48.7, 45.9, 31.2; HRMS (FAB) m/z 375.1693 (M+H)+ (C23H22N2O3 requires 375.1709); Anal. (C23H22N2O3 ·2HCl·4H2O) C, H, N.

Provenance & Evidence