Indole derivatives. X. 5-Acetyl-a-methyltryptamine.
Terzyan, A. G.; Tatevosyan, G. T.
Khim. Nauki (1962), 15(6), 563-6.
Journal written in Russian.
CAN 59:35470 AN 1963:435470
Abstract
5-Acetyl-a-methyltryptamine (I) was prepd. for study of its biol. properties. Prepn. of 2,3-dioxo-6-methylpiperidine 3-p-acetylphenylhydrazone (II): 0.1 mole 6-methyl-3-carbethoxy-2-piperidone and 6 g. KOH in 250 ml. H2O kept overnight at room temp. filtered, the soln. cooled to -5° and 500 ml. cold soln. of p-acetylphenyldiazonium chloride (prepd. from 13.5 g. p-aminoacetophenone, 7.6 g. NaNO3, and 28 ml. concd. HCl) added portionwise, pH adjusted to 4.5 by addn. of 40 ml. AcONa soln., the whole stirred 4 hrs., kept overnight, the orange ppt. filtered off, washed with H2O, dried, and triturated with Et2O, then with 50% EtOH to yield 75.2% II, light-yellow after boiling with C, m. 225-6° (EtOH). Synthesis of 3-oxo-5-methyl-10-acetyl-3,4,5,6-tetrahydro-b-carboline (III): 0.05 mole II and 60 ml. 85% HCO2H refluxed 5 hrs., cooled, filtered off, washed with H2O, and airdried gave 85.1% III, m. 345-6° (EtOH) (decompn.). III (0.035 mole), 36 g. KOH, and 550 ml. 60% EtOH was boiled 15 hrs., 200 ml. H2O added, EtOH removed, the residue filtered, the filtrate acidified with AcOH to pH 6, the ppt. filtered off, washed with H2O, and air dried to give 98.2% colorless 5-acetyl-a-methyltryptamine-2-carboxylic acid (IV), m. 329-30° (H2O) (decompn.). IV (0.025 mole) in 170 ml. 25% HCl and 50 ml. AcOH refluxed 36-40 hrs., filtered, the filtrate basified with NaOH, I filtered off, washed with H2O, dried over KOH, extd. with Et2O several times, and most of Et2O evapd. gave 54% I, m. 146-8°, hydrochloride m. 234-5° (Et2O), picrate m. 150°. Cf. CA 59, 2753e.
Do Your Part To Win The War