Phenethylamine → N-phenethyl 4-benzyloxy-1-methyl-1H-indole-2-carboxyamide

Participants

Reaction Steps

To a solution of 4-benzyloxy-1-methyl-1H-indole-2-carboxylic acid (0.20 g) in DMF (10 mL) was added TBTU (0.23 g), HOBt (0.11 g) and DIEA (0.27 mL). After 5 min., phenethylamine (0.11 mL) was added and stirring was continued overnight under nitrogen at room temperature. The residue remaining after DMF evaporation was dissolved in EtOAc; washed with dilute HCl, saturated NaHCO3, and brine; dried over MgSO4; and concentrated at reduced pressure to give the intermediate product N-phenethyl 4-benzyloxy-1-methyl-1H-indole-2-carboxyamide (0.18 g) which was used without further purification. Hydrogenation of this product by a method analogous to that described in Example 9 give 0.14 g of the title compound. MS CI (M++H)=295.

Provenance & Evidence