Ammonium Chloride → HCID 131715773, compound

Participants

Reaction Steps

A Grignard reagent was prepared from 4-methoxybutyl bromide (5 g) and magnesium (0.72 g) in dry ether (25 ml). After cooling with an ice-bath, under a blanket of nitrogen, a solution of 8-chloro-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one (2.2 g) in dichloromethane (25 ml) was added slowly. When addition was complete the mixture was stirred at room temperature for 3 hours. It was poured onto saturated aqueous NH4Cl, the layers were separated and the aqueous phase extracted with dichloromethane. The combined organic phases were washed with water and dried (MgSO4). Filtration and evaporation gave an orange solid, which was triturated with boiling ethyl acetate, cooled, filtered and the crystals were washed with hexane. The crystals were suspended in boiling ethanol and acidified with ethanolic HCl. Evaporation of the solution gave a solid which crystallised from isopropanol. Two crops were combined and dried at 50°/1 mm to give pure 8-chloro-10-hydroxy-10-(4-methoxybutyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indole, hydrochloride quarter hydrate (2.28 g) as buff-cream crystals, m.p. 218°-221° (dec).

Provenance & Evidence