反应详情

4-Nitro-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide was prepared from 15 g. (0.085 mole) of 1-cyclohexyl-3-methylaminopyrrolidine and 15 g. (0.08 mole) p-nitrobenzoyl chloride. The 4-nitro-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide was converted to the fumarate salt (8.4 g., 24%) by precipitation with fumaric acid from isopropanol-isopropyl ether. The fumarate salt was dissolved in 95% ethanol and hydrogenated at three atmospheres of hydrogen over Raney Nickel for about two hours. The mixture was filtered, the filtrate concentrated and the residue partitioned between dilute sodium hydroxide and chloroform. The chloroform layer was dried and concentrated and the residue treated with hexamic acid in isopropanol-isopropyl ether. Recrystallization from the same solvent gave 5.2 g. (13.5% overall) of the salt melting 196°-199° C.

1. customThe 4-nitro-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide was converted to the fumarate salt (8.4 g., 24%) by precipitation with fumaric acid from isopropanol-isopropyl ether
2. dissolutionThe fumarate salt was dissolved in 95% ethanol
3. filtrationThe mixture was filtered
4. concentrationthe filtrate concentrated
5. customthe residue partitioned between dilute sodium hydroxide and chloroform
6. dry with materialThe chloroform layer was dried
7. concentrationconcentrated
8. additionthe residue treated with hexamic acid in isopropanol-isopropyl ether
9. customRecrystallization from the same solvent
10. customgave 5.2 g
11. custommelting 196°-199° C.