Phenol → HCID 67436641, compound

Participants

Reaction Steps

4.7-dichloroquinoline (0.29 g), 1 g of phenol and 0.6 g of impure (containing 1-aminoadamantane) 3-adamantylaminopropylamine were heated at 120° C. for 3 hours. By g.c-m.s. analysis it was found that the mixture contained besides the aimed—at product, 1-aminoadamantane, some 4.7-dichloroquinoline and a product which is by its mass spectrum 7-chloro-4-adamantylaminoquinoline (M+=312.5). The mixture was dissolved in several ml of methanol, poured into 50 ml of 10% KOH and extracted with t-butyl methyl ether (2×50 ml). The combined extracts were brought to dryness, the residue dissolved in a mixture of N(C2H5)3, little (CH3)3COCH3 and some methanol, transferred to a column (5 cm. diameter, Kieselgel, wetted with N(C2H5)3: (CH3)3OCH3: CH3OH=125:75:5 (by volume) and eluted with 205 ml of this solvent. The solvent was changed to N(C2H5)3: (CH3)3OCH3:CH3OH=100:100:10 (by volume), and the product together with M+=151 (adamantylamine) was eluted, +another by-product (by g.c.-m.s. perhaps 7-chloroquinolone, which was not in the crude product prior to base-treatment). After re-elution (30 g Kieselgel, N(C2H5)3: CH3OH=200:5, fraction collection and their g.c-m.s. analysis), 33 mg of pure 7-chloro-(3-adamantylamino)-aminopropylquinoline was obtained as a white solid. Yield=6% of theory. G.c.-m.s. (DB5-column, 30 m, injection block temperature=250° C., t0=150° C./2 min, then 11° C./min.→280° C., Rt=24.05 min.): M(35Cl, 37Cl)+=369 (24%), 371 (9%), 135, C10H15+, (100%).

Provenance & Evidence