Ring opening of cyclic salicylamides

✍ Scribed by Barrie M. Phillips; Herbert J. Havera; Toni L. Hammes

• Publisher: John Wiley and Sons
• Year: 1969
• Tongue: English
• Weight: 315 KB
• Volume: 58
• Category: Article
• ISSN: 0022-3549
• DOI: 10.1002/jps.2600581128

✦ Synopsis

I 4 : p 8 0 5 10 0 5 m i n Figure 1-Gas chromatogram of (left) phenolic; (right) nonphenolic alkaloid fraction of Echinocereus merkeri. Column: 1.83 m. (6 f t . ) X 0.41 cm. (0.125 in.); 5% SE-30 on Gas Chrom P ; initial temp. 130",progr. 6"lmin. Peak I = hordenine, peak 2 = 3-methoxytyramine, peak 3 = unknown, peak 4 = N,N-dimethyl-3,4-dimethoxyphenethylamine, peak 5 = salsoline, peaks 6-7 = unknowns, peak 8 = unknown (M+ = m/e 140, base peak = 58), penk 9 = mixture of N-methyl-and N,N-dimethyl-3,4-dimethoxyphenethylamine.

acc. to Brockmann) and eluted with the solvents shown in Table I.

The eluates were investigated by TLC and GLC using SE-30 and XE-60 columns (1). N,N-Dimethyl-3,4-dimethoxyphenethylamine, and N-methyl-3,4-dimethoxyphenethylamine, were isolated using preparative column chromatography, and recrystallized as hy-drochlorides from hot chloroform upon the dropwise addition of ether. Melting points ofhydrochlorides, Reported (1) m.p.'s for these compounds are 194-197" and 196-197 ', respectively.

Mass spectra were recorded with a gas chromatograph mass spectrometer (LKB9000), ion source 270", electron energy 70 eV., and ionization current 60 pamp. Mass spectrometric data; compounds IV-V, see Reference 4. N-Methyl-3,4-dimethoxyphenethylamine, major peaks, mle 44 (loox), 151 (3%), 152 (40%), 195 (M+ 1%). N,N-Dimethyl-3,4dimethoxyphenethylamine, major peaks, mle 58 (loo%), 151 (373, 152 ( l x ) , 209 (Mf 1%). Salsoline, major peaks, mle 149 (3%h 153 (7%), 154 (473, 178 (1m%), 192 (6%), 193 (M+, 3%).