Succinic anhydride → N-Benzyloxy-N-(4-cyanobutyl)succinamic acid

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Reaction Conditions

Reaction Steps

N-Benzyloxy-N-(4-cyanobutyl)succinamic acid (6) was synthesized by charging a flask with 2.8 g (13.7 mmol) of (5) in 23 mL of pyridine and 2.1 g (20.8 mmol) of succinic anhydride, heated at 100° C. for 1.5 hours and then allowed to cool to room temperature and to stir overnight. The pyridine was removed under vacuum and the residue was dissolved in a is minimal amount of chloroform and filtered. The chloroform was removed and the residue was dissolved in ether, which was extracted three times with 20% potassium bicarbonate (3×50 mL). The aqueous solutions were combined, acidified and extracted with ether. This solution was dried over anhydrous sodium sulfate, filtered and evaporated. The residue was then chromatographed on 70-230 mesh silica gel by eluting with 5% methanol in chloroform to give 4.12 g (98%) of (6): NMR δ 1.56-1.7 (m, 2 H), 1.7-1.97 (m, 2 H), 2.36 (to 2 H), 2.60-2.80 (m, 4 H); 3.68 (t, 2 H), 4.85 (s, 2 H), 7.4 (s, 5 H); IR (CHCl3) 3670, 2930, 2240, 1710, 1650, 1415, 1200 cm-1. Anal. calcd. for C16H20N2O4 : C, 63.17; H, 6.64. Found: C, 63.36; H, 6.74. A sample of (6) was crystallized from hexane/EtoAc, mp 71° C.

Provenance & Evidence