N-3-Bromopropylphthalimide → HCID 20081633, compound

Participants

Reaction Conditions

Reaction Steps

In an argon stream with ice cooling, a solution of 2.3 g of the 1-(3-hydroxybenzyl)-2-piperidone obtained in Reference Example 2 in 10 ml of N,N-dimethylformamide was added dropwise to a soltuion of 0.44 g of 60% sodium hydride in 5 ml of N,N-dimethylformamide. Subsequently, a solution of 2.8 g of N-(3-bromopropyl)phthalimide in 10 ml of N,N-dimethylformamide was added dropwise to the mixture at room temperature, followed by stirring at 65° C. for 8 hours. The resulting mixture was cooled, ice-cold water was thereafter added thereto, the mixture was subjected to extraction with diethyl ether, 6N hydrochloric acid was then added to the organic layer for extraction into the aqueous layer, and the aqueous layer was made alkaline with sodium hydroxide, followed by extraction with diethyl ether again. The organic layer was dried over magnesium sulfate and thereafter distilled to remove the solvent, giving N-[3-[3-(2-oxopiperidinomethyl)-phenoxy]propyl]phthalimide. This compound was hydrolyzed with hydrazine in the same manner as in Example 1, (ii) to afford 1.4 g of 3-[3-(2-oxopiperidinomethyl)phenoxy]propylamine (yield 51% ).

Provenance & Evidence