反应详情

4-(Aminomethyl)benzoic acid (3.6 g) is suspended in methylene chloride (100 mL), to which 15 mL triethylamine is added. Chlorotrimethylsilane (10 mL) is then added and the mixture allowed to stir at room temperature for 1 hr. The mixture is then cooled in an ice bath and 4-phenylbutyryl chloride (5.3 g) in methylene chloride (10 mL) is added dropwise and the resulting mixture stirred for 30 min at 0° C., followed by an additional 3 hrs at ambient temperature. The mixture is treated with 75 mL 1N HCl, after which the organic layer is separated and extracted with 1N HCl. The precipitate which had formed is recovered by filtration and recrystallized two times from methanol/1N HCl to give pure N-(4-carboxybenzyl)-4-phenylbutyramide.

1. additionis added
2. temperatureThe mixture is then cooled in an ice bath
3. stirringthe resulting mixture stirred for 30 min at 0° C.
4. waitfollowed by an additional 3 hrs at ambient temperature
5. customafter which the organic layer is separated
6. extractionextracted with 1N HCl
7. customThe precipitate which had formed
8. filtrationis recovered by filtration
9. customrecrystallized two times from methanol/1N HCl