Succinic anhydride → 1-Hexadecanamine, 3,7,11,15-tetramethyl-

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Reaction Steps

Phytylamine (2.32 g), succinic anhydride (1.16 g) and pyridine (10 ml) was stirred at room temperature for 48 hours. Most of the pyridine was removed under reduced pressure and the crude product dissolved in dichloromethane and washed with 2M HCl (2×100 ml). The organic was layer separated, dried (MgSO4) and concentrated in vacuo to dryness. The crude product was chromotographed (ethyl acetate as eluant) to give phytanamine hemisuccinamide 1.23 g (91%) as a thick liquid which solidified on standing 1H-n.m.r. (CDCl3) δ0.8-1.8 (m, 39H), 2.5 (m, 2H, CH2COO—), 2.6 (m, 2H, CH2COOH), 3.2 (m, 2H, CH2N—), 5.79 (b, 1H, NH), m/z (CI, CH4), 412 (M+)

Provenance & Evidence