Hydrogen Bromide → HCID 19099734, compound

Participants

Reaction Steps

cis-5-Methoxy-1-methyl-2-(di-n-propylamino)tetralin hydrochloride (150 mg, 0.48 mmol) was heated in 48% aqueous HBr for 2 h at 120° C. under N2. The volatiles were evaporated in vacuo and the residue was applied to pre-coated PLC plates (silica gel 60 F254, Merck) which were eluted with CHCl3 -MeOH (9:1). After elution of the product the volatiles were evaporated in vacuo and the residue was recrystallized at least twice. giving cis-hydroxy-1-methyl-2-(di-n-propyl-amino)tetralin.Hbr (66 mg, 48%) of an isomeric purity >95% (GC, 225° C.) IR (KBr) ν3136 cm-1 (O-Hstr); NMR (MeOH-d4), δ1.05 (t,6H), δ1.31 (d,3H), δ1.50-3.74 (m,14H), δ6.44-6.69 (m,2H), δ6.81-7.07 (m,1H); MS (70 eV) m/z 261 (36%), 232 (100%), 161 (82%).

Provenance & Evidence