1-Heptanamine → HCID 54427198, compound

Participants

Reaction Steps

To a solution consisting of 3-methyl-1-(propyl-4-pyridinylamino)-1H-indol-5-ol (2.23 g) and tetrahydrofuran (53 ml) was added 1,1'-carbonyldiimidazole (2.57 g) at room temperature with stirring under nitrogen. Stirring was continued for 96 hours, at which time acetic acid (1.54 ml) was added. To the resulting reaction mixture was added a solution consisting of heptyl amine (1.76 ml), acetic acid (0.71 ml) and THF (5 ml). After stirring for 24 hours, an additional solution of heptyl amine (1.17 ml), acetic acid (0.48 ml) and THF (5 ml) was added and stirring continued for 3 hours. The reaction mixture was poured into a dilute aqueous sodium bicarbonate solution and the product extracted with ether (3x). The combined organic layer was washed with brine and dried (MgSO4). Filtration, concentration and purification via flash column chromatography (silica gel, 2% Et3N/ether) afforded 1.60 g of the desired carbamate after recrystallization from ether/pentane, m.p. 102°-104° C.

Provenance & Evidence