An Improved Synthesis of 8‐Amino‐2‐methyl‐4‐phenyl‐1,2,3,4‐Tetrahydroisoquinoline
The regioselectivity of the reaction of 2‐nitrobenzylmethylamine (1) and styrenoxide (2) leading to a mixture of the isomeric aminoalcohols 3a and 3b has been studied. The course of the reaction strongly depends on the type of the solvent used as reaction medium. The highest selectivity (3a:3b = 9:1) was achieved with a combination of polar aprotic and protic solvents (DMFA and ethanol). 1H n.m.r. spectroscopy was used for identification of the isomers as well as for the determination of their ratio in the crude reaction mixtures. The isomer ratio remains unaffected during catalytic reduction (Ra‐Ni) of 3a/3b to a mixture of the corresponding aminoalcohols 4a and 4b. Pure 3a, 4a and 4b were independently synthesized for comparison. Cyclodehydration of crude 4a/4b mixtures gives 5 in a very good yield.
Reaction of Benzazepines with Phenyloxiranes
The reaction between the 7,8‐dimethoxy‐1‐phenyl‐2,3,4,5‐tetrahydro‐1H‐3‐benzazepines ( ± )‐1, (1S)‐(−)− 1 und (1R)−( + )− 1 and racemic or optically active phenyloxiranes 2a–d leads to a mixture of the regioisomcric carbinoles 3a–d and 4a–d, respectively. In all cases the reaction is not stereospecific, but regiospecific with regard to the p‐phenyl substituted phenyloxiranes 2b–d. The ratio of the isomers was determined by HPLC and the structures of the regioisomers 3a and 4a were deduced from the 1H‐n.m.r. spectra. The newly synthesized carbinols proved to be strong re‐uptake in hibitors of the monoamines dopamine (DA), norepinephrine (NE) and serotonine (5‐HT).
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