Ammonium Chloride → HCID 14181391, compound

Participants

Reaction Steps

A solution of 1-bromo-3-methoxybutane (6.0 g) in dry ether (20 ml) was added dropwise under a nitrogen atmosphere to magnesium turnings (0.9 g) at such a rate as to maintain gentle reflux. After stirring at reflux for 0.5 hour the reaction mixture was chilled in ice and a solution of 9-chloro-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one (3.5 g) in dry 1,2-dichloroethane (100 ml) was added dropwise. After stirring the reaction mixture for one hour at room temperature it was cooled and excess saturated ammonium chloride solution was added dropwise. The organic phase was separated and the aqueous phase was extracted with chloroform. The extracts were combined with the organic phase, dried (MgSO4) and the solution evaporated under reduced pressure to leave an oil which was triturated with ether to give a solid. Recrystallisation from ethyl acetate gave the title compound as colourless needles m.p. 164°-5°. Treatment of a solution of these needles in methanol with ethereal hydrogen chloride, followed by evaporation in vacuo gave a solid which was recrystallised from propan-2-ol to give the title compound as the hydrochloride, colourless crystals (2.81 g) m.p. 264°-5°.

Provenance & Evidence