Lithium diisopropylamide → HCID 22992262, compound

Participants

Reaction Steps

The 1-(4-oxanyl)-1-(3-pyridyl)methylamine was synthesized essentially according to the procedure described above for the synthesis of 1-(3-oxolanyl)-2-(3-pyridyl)ethylamine. Thus, 4-oxanyl methanesulfonate (0.99 g, 5.5 mmol), prepared according to the procedure of Suto et al., J. Med. Chem., 34: 2484 (1991), was treated with the imine anion generated by reacting N-(diphenylmethylidene)-3-(aminomethyl)pyridine (1.36 g, 5.0 mmol) with LDA (5.5 mmol in 5.0 mL THF). A work up similar to the one described for the synthesis of 1-(3-oxolanyl)-2-(3-pyridyl)ethylamine, followed by purification by column chromatography (15% methanol in chloroform), yielded 1-(4-oxanyl)-1-(3-pyridyl)methylamine (499 mg, 52% yield).

Provenance & Evidence