Hydrochloric Acid → HCID 69948262, compound

Participants

Reaction Steps

To a solution of 5-(2,3-dihydropyran-2-yl)-3-(2-pyrrolidinylethyl)-1H-indole (Example 20b, 0.049 g, 0.165 mmol) in absolute ethanol (5 mL) was added NaBH3CN (0.496 mmol) and methanolic HCl [prepared from acetyl chloride (2 mL) and methanol (10 mL)] alternately. The mixture was allowed to stir for 3 hours at which time the reaction was quenched with sodium bicarbonate (sat.) and the product was extracted three times with CH2Cl2. The organic layer was dried (NaSO4), filtered and concentrated. The crude product was purified by column chromatography (7% NH3 in CH2Cl2) to yield the title compound 0.029 g, 59%) as a clear oil; HRMS-FAB+ for C19H26N2O: calc. MH+ : 99.2123; found MH+ :299.2159.

Provenance & Evidence