1967 年 87 巻 5 号 p. 563-569
Syntheses of sendaverine and its related compounds were carried out, and their infrared and NMR spectra were examined. It was thereby found that the infrared spectra of 13 kinds of 2-substituted 1, 2, 3, 4-tetrahydroisoquinoline derivatives, excluding XX and the N-methylated compound, show characteristic absorption band very similar to the Bohlmann band which is considered to be the characteristic absorption of trans-quinolizidine. In the NMR spectra of these compounds, the proton signals of the methylene groups in 3- and 4-positions show a characteristic broad, singlet-like absorption, irresuctive of the substituent on the ring-nitrogen or on the benzene ring, as long as there are substituents like methoxyl, beozyloxyl, and hydroxyl group in the 6- or 7-position and the substituent in the 2-position is a unit higher than ethyl or benzyl group, but not methyl group.