Hydrochloric Acid → 4-(6-Chloronaphthalene-2-sulfonyl)-1-{methyl[1-(4-pyridyl)-4-piperidinyl]amino}-2-piperazinone

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Reaction Steps

1-{[1-(tert-Butoxycarbonyl)piperidinyl]methylamino}-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (1.63 g) was combined with methanol (10 ml) and a 4N solution of hydrochloric acid in ethyl acetate (15 ml) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue obtained was combined with 4-chloropyridine hydrochloride (950 mg), triethylamine (3.8 g) and ethanol (100 ml), and reacted in a sealed tube at 150° C. for 15 hours. The reaction mixture was concentrated and the residue was combined with a 1N aqueous solution of sodium hydroxide, extracted with dichloromethane, dried and concentrated. The residue obtained was purified by a column chromatography (dichloromethane: 10% aqueous ammonia-containing methanol=20:1) and crystallized from ether to obtain the title compound (794 mg) as colorless crystals.

Provenance & Evidence