Hydrogen Bromide → Eletriptan Hydrobromide

Participants

Reaction Steps

49% w/w Hydrobromic acid (432 mg, 0.3 ml, 2.6 mmol) was added to a stirred solution of 3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethyl)-1H-indole (1.0 g, 2.6 mmol) in acetone (10 ml) at room temperature. After a further 15 minutes, the reaction mixture was evaporated under reduced pressure to give a yellow liquid; the residual water therein was then azeotropically removed using 2-propanol. The resulting cloudy, yellowish oil (1.55 g) was triturated with ether and then dissolved in hot 2-propanol (25 ml); this solution, on cooling, provided the title compound (1.13 g) as a pale yellow crystalline solid after filtration, washing with 2-propanol and drying in vacuo, m.p. 165-170° C. Found: C,56.67; H,5.78; N,5.82. C22H26N2O2S; HBr requires C,57.02; H,5.87; N,6.04%.

Provenance & Evidence