foxy2 (Distinctive Doe) 11-01-01 21:53 No 231961 |
Alternate AMT from Gramine Procedure (Rated as: excellent) |
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Indole derivatives. XLIV. Synthesis of indopan [3-(2-aminopropyl) indole] from indole. Bulatova, N. N.; Suvorov, N. N. Khim.-Farm. Zh. (1968), 2(2), 27-9. Journal written in Russian. CAN 69:77044 AN 1968:477044 Abstract Na (0.42 g.) dissolved in 15 ml. abs. EtOH, 95 ml. abs. iso-PrOH, 4.1 g. EtNO2, and 2.9 g. 3-dimethylaminomethylindole added dropwise with intensive stirring, after 20 min. 4.2 g. Me2SO4 in 30 ml. iso-PrOH added, the mixt. stirred at room temp. 1-2 hrs., treated with 300-500 ml. water, extd. with ether, and the product chromatographed and sepd. with 5:1 Et2O-petroleum ether gave 91% 3-(2-nitropropyl)indole (I), b1 174-6°. a-Methyltryptamine (II), m. 96-8°, was synthesized in 67.2% yield by hydrogenation of I in EtOH in the presence of Raney Ni at 60° at a starting pressure of 50 atm., filtration after 2-4 hrs. and evapn. in vacuo; II hydrochloride (indopan) m. 214-15°; II adipate m. 223-4° (EtOH); II picrate, red, m. 218-19°. Do Your Part To Win The War |
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foxy2 (Distinctive Doe) 11-01-01 22:10 No 231969 |
Re: Alternate AMT from Gramine Procedure | Bookmark | ||||||
Indole derivatives. XLVIII. Synthesis and pharmacological properties of N-L-a'-glutamyl-a-ethyltryptamine. Bulatova, N. N.; Trubitsyna, T. K.; Suvorov, N. N.; Mashkovskii, M. D. Khim.-Farm. Zh. (1968), 2(11), 6-9. CODEN: KHFZAN Journal written in Russian. CAN 70:58253 AN 1969:58253 Abstract PrNO2 (16.8 g.) and gramine (10.2 g.) were added to a soln. of NaOEt (1.46 g. Na and 30 ml. abs. EtOH) and poured into 310 ml. iso-PrOH. After 25 min. 14.6 g. Me2SO4 in 90 ml. iso-PrOH was added at (less than)35° yielding (overnight) 91% 3-(2-nitrobutyl)-indole (I), m. 90-2°. Hydrogenation of I in the presence of Raney Ni in EtOH at 60° beginning at 50 atm. 3-4 hrs. yielded 9.5 g. a-ethyltryptamine (II), m. 104-5° (aq. MeOH). I hydrochloride, adipate, and picrate had m.ps. 218-19°, 212-13° (EtOH), and 202°, resp. Carbobenzoxy-L-glutamic acid g-benzyl ester (III) prepd. by the method of Hanby et al. (1950) was dissolved in 80 ml. dry tetrahydrofuran (THF), 5.6 ml. Et3N was added at -8 to -10°, followed by 5.6 ml. iso-BuO2CCl and finally 6.58 g. II in 150 ml. THF. Stirring followed by workup yielded (73%) carbobenzoxy-L-a'-glutamyl-a-ethyltrypta Do Your Part To Win The War |
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foxy2 (Distinctive Doe) 11-01-01 22:19 No 231973 |
Re: Alternate AMT from Gramine Procedure | Bookmark | ||||||
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-tetrahy Do Your Part To Win The War |
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