Tetrahydrofuran → 4-Dipropylaminomethyl-aniline

Participants

Reaction Steps

The compound (2.61 g) obtained in Example 15-1 was dissolved in methanol (25 ml). The solution was added with THF (13 ml), activated carbon (261 mg), and iron trichloride hexahydrate (26.1 mg) and the whole was refluxed for 30 minutes. After having been cooled to room temperature, the solution was added with hydrazine monohydrate (1.88 ml) and then the whole was refluxed for 3 hours. After completion of the reaction, the resultant was subjected to filtration through Celite. The filtrate was subjected to extraction with chloroform and washed with distilled water and a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (865 mg) as a yellow oily substance.

Provenance & Evidence