Ammonium Hydroxide → 4-Amino-5-chloro-2-methoxy-N-(tetrahydro-1H-pyrrolizin-7a(5H)-ylethyl)benzamide

Participants

Reaction Steps

4-Amino-5-chloro-2-methoxybenzoic acid (1.0 g, 0.005 moles) and 1,1'-carbonyldi-imidazole (892 mg, 0.00055 moles) were suspended in the DMF (10 ml) and the mixture was stirred until solution occurred (three hours). At this time, tetrahydro-1H-pyrrolizin-7a(5H)-ethylamine [amine Heterocycles 16, 755, 1981](771 mg; 0.005 moles) was added and the mixture was stirred for 1 hour. Tlc 30% MeOH/CHCl3 /1/10% NH4OH indicated that the reaction was complete. Concentration afforded a residue which was partitioned between Et2O/H2O. The product crystallized. The solid was filtered and dissolved in CHCl3, washed with dilute K2CO3, dried over MgSO4 and concentrated to a solid. The solid was triturated with Et2O and converted to the HCl salt with MeOH/HCl to yield 1.27 g (69%) of the product.

Provenance & Evidence