Pyridine → N-Benzylacetamide

Participants

Reaction Steps

To a suspension of P-HOBT 1 (0.212 g, 0.125 mmol) in CH2Cl2 (5 mL) was added acetic anhydride (0.216 g, 0.200 mL, 2.12 mmol, 17 equiv.) and pyridine (0.234 g, 0.240 mL, 2.96 mmol, 24 equiv.). The suspension was subsequently rocked for 60 minutes at 25° C. The polymer was then filtered and washed with CH2Cl2 (3×5 mL), NMP (3×5 mL), CH2Cl2 (3×5 mL), and anhydrous Et2O (3×5 mL). The polymer was re-suspended in CH2Cl2 (5 mL) and benzylamine (0.0098 g, 0.010 mL, 0.91 mmol, 0.73 equiv. based on P-HOBT) was added. The suspension was rocked at 25° C. for 4 h. The polymer was then filtered and washed with CH2Cl2 (4×5 mL). The filtrate and washings were combined and concentrated to yield 0.014 g (100%) of N-benzylacetamide as a white solid.

Provenance & Evidence