Diethyl Ether → HCID 178507584, compound

Participants

Reaction Steps

Palladium (II) acetate (519 mg) and an aqueous solution (23 ml) of potassium fluoride (2.69 g) was added at room temperature to a solution of 6-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyridin-3-amine (3.0 g) described in Reference Example 78 in tetrahydrofuran (115 ml), poly(methylhydrosiloxane) (2.8 ml) was added dropwise and the mixture was stirred at the same temperature for an hour. After completion of the reaction, diethyl ether (115 ml) was added, the reaction solution was filtered through Celite and the filtrate was concentrated. Saturated brine was added to the resulting solution and extracted with ethyl acetate three times. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with NH silica gel column chromatography (n-hexane/ethyl acetate) to give cis-6-[4-(morpholin-4-yl)cyclohexyl]pyridin-3-amine (1.45 g) and trans-6-[4-(morpholin-4-yl)cyclohexyl]pyridin-3-amine (906 mg) as a white solid respectively.

Provenance & Evidence