3-(Dimethylamino)propyl chloride hydrochloride → 2-(3-(4-Naphthylpiperidyl)propyl)isoindoline Hydrochloride

Participants

Reaction Steps

Using 4-(1-naphthyl)piperidine (124 mg, 0.50 mmol) and 2-(3-chloropropyl)isoindoline hydrochloride (139 mg, 0.72 mmol) instead of 4-(3-indolyl)piperidine and 3-dimethylaminopropyl chloride hydrochloride respectively, reaction, extraction, and concentration were carried out in the same procedure as Example 4. The resulting crude product was purified by column chromatography on a silica gel (silica gel NH-DM 1020 produced by Fuji Silysia Chemical Ltd., eluent; chloroform:methanol=20:1) to afford a free form (158 mg) of the title compound as a yellow viscous oil. After adding hydrochloric acid/methanol to a solution of the free form in methanol, the mixture was concentrated and was then recrystallized from methanol/ether to afford the title compound (91 mg, yield: 44%) as white crystals.

Provenance & Evidence