Formaldehyde → Succinimide, N-(p-phenetidinomethyl)-

Participants

Reaction Steps

(4-Ethoxy-phenyl)-methyl-amine: A mixture of 2 g (14.57 mmol) of 4-ethoxy-phenylamine, 1.73 g (17.49 mmol) of succinimide, and 1.4 mL (17.49 mmol) of 37% aq formaldehyde in 15 mL of EtOH was heated at reflux for 18 hours. The reaction mixture cooled down and precipitate was filtered and washed with Et2O, dried to give 2.89 g (11.27 mmol) of 1-[(4-ethoxy-phenylamino)-methyl]-pyrrolidine-2,5-dione, which was dissolved in DMSO and treated with 0.428 g (11.27 mmol) of NaBH4. The reaction mixture was heated in a hot water bath for 15 min, then it was poured into 20 mL of cold water and extracted with Et2O (3×15 mL), the organic extracts were combined and concentrated to give 1.7 g of the title compound. LC-MS (ESI+; 152 ([M+H]+)).

Provenance & Evidence