Hydrochloric Acid → HCID 67618169, compound

Participants

Reaction Steps

In a 500 ml Parr hydrogenation bottle, 10% Pd/C (1.5 g) was suspended in 50 ml ethanol, and to this was added a solution of 1-[(3-fluoro-4-pyridinyl)propylamino]-5-phenylmethoxy-1H-indole (15.0 g) in 200 ml ethanol. The mixture was shaken under 50 psi hydrogen gas for three hours at 50° C. Upon cooling, the mixture was filtered, and the filtrate was concentrated to give a solid, 11.4 g. This material was eluted on a silica gel column with ethyl acetate/dichloromethane (1:3) via HPLC, and the desired fractions were concentrated to give a solid, 8.5 g, m.p. 90°-95° C. A 2.0 g sample of this material was dissolved in 50 ml methanol, the pH was adjusted to 1 with ethereal HCl, and the solution was diluted with 200 ml ether. The resultant precipitate was collected and dried to give 2.1 g of the product, m.p. 218° C. (dec.).

Provenance & Evidence