Raasch, Maynard S. published the artcileChemistry of sulfur tetrafluoride. IX. Reaction with amino acids in hydrogen fluoride, Name: 1,1,1-Trifluoropropan-2-amine, the publication is Journal of Organic Chemistry (1962), 1406-9, database is CAplus.
cf. Smith, CA 55, 6419i. SF4 (I) converted the CO group in amino acids to a trifluoromethyl group when the reaction was carried out in HF. When an optically active amino acid was used, optical activity was retained in the resulting fluoro amine. Picolinic, nicotinic, and isonicotinic acids were converted into the Na salts of pipecolic, nipecotic, and isonipecotic acids by dissolving 100 g. of the acid in 300 ml. H2O containing 33 g. NaOH and charging the solution and 3 g. Ru-C into a bomb, hydrogenating 9 hrs. at 120¡ã, filtering, evaporating, and drying the Na salt 16 hrs. at 90¡ã. Heating 95 g. dodecylamine and 18.5 g. 2-chloropropionic acid 15 hrs. at 100¡ã gave 19 g. N-dodecyl-DL-alanine, m. 210-13¡ã (AcOH-H2O). The general procedure was to heat 8 hrs. at 120¡ã 0.4 equivalent of the amino acid, 50 g. HF, and 100 g. I in a shaker tube. p-Aminobenzoic acid (14 g.), 100 g. HF, and 30 g. I heated 4 hrs. to 125¡ã then maintained 6 hrs. gave 37% p-aminobenzotrifluoride. With 2-aminobutyric acid, addnl. HF did not raise the low yield. In the absence of HF, I converted nicotinic acid to nicotinoyl fluoride in 50% yield, b6 50-2¡ã. This was easily hydrolyzed by H2O. Except for the picolines, the reaction products were poured into a dish and heated to expel HF. The residue may be transferred to a steam distillation apparatus and steam distilled For the lower amines it was best to isolate as the hydrochloride. In the case of the products from simple aliphatic amino acids, the residue remaining after evaporation of HF stirred with H2O, filtered, and the filtrate evaporated gave the solid amine-HF. The amine was liberated by addition of 40% KOH. The trifluoromethylpicolines were volatile and such weak bases that evaporation of the reaction mixture, unless carefully done, gave the free picoline. Hence, it was diluted with 75 ml. H2O, made basic, the mixture steam distilled, and the oil separated The product obtained from quinaldie acid was warmed to expel most of the HF, the residue stirred with H2O, crystalline 2-(trifluoromethyl)quinoline collected, and recrystallized from hexane. The product from 4,5-imidazoledicarboxylic acid was similarly treated. The following fluoro amines were thus obtained (product, starting amino acid, % yield, b.p., n25D, and pKa given): CF3CH2NH2, glycine, 24, 36¡ã, 1.3004, 5.6; CF3(CH2)2NH2, ¦Â-alanine, 41, 67.5-8.0¡ã, 1.3270, 8.6; CF3(CH2)3NH2, 4-H2N(CH2)3CO2H, 7.1, 90-1¡ã, 1.3452, 9.6; MeCH(CF3)NH2, DL-alanine, 29, 46-7¡ã, 1.3180, 5.8; EtCH(CF3)NH2, DL-2-aminobutyric acid, 3.5, 65-6¡ã, -, 5.7; PrCH(CF3)NH2, DL-norvaline, 2.5, 87-8¡ã, 1.3568, 5.7; BuCH(CF3)NH2, DL-norleucine, 14, 113-16¡ã, 1.3635, 5.7; Me(CH2)5CH(CF3)NH2, DL-2-aminooctanoic acid, 39, 158-60¡ã, 1,3825, -; Me2C(CF3)NH2, 2-methylalanine, 35, 54¡ã, 1.3305, 5.8; iso-PrCH(CF3)NH2, DL-valine, 4.2, 83-4¡ã, 1.3540, 5.6; iso-PrCH2CH(CF3)NH2, L-leucine, 22, 103-4¡ã, 1.3610, 5.6; CF3(CH2)2CH(CF3)NH2, L-glutamic acid, 12, 106¡ã, 1.3222, 4.7; MeS(CH2)2CH(CF3)NH2, DL-methionine, 1.5, 160-2¡ã, 1.4260, 4.8; MeCH(CF3)NH(CH2)11Me, N-dodecyl-DL-alanine, 61, 74-6¡ã/0.18 mm., 1.4119, -; PhCH2CH(CF3)NH2, DL-phenylalanine, 3.6, 53-5¡ã/1 mm., 1.4613, -; p-CF3C6H4NH2, p-H2NC6H4CO2H, 37, 85¡ã/14 mm., -, -; 2-CF3C5H10N, Na DL-pipecolate, 9.6, 122-4¡ã, 1.3905, 6.4; 3-CF3C5H10N, Na DL-nipecotate, 40, 128-30¡ã, 1.3910, 8.7; 4-CF3C5H10N, Na isonipecotate, 34, 133¡ã, 1.3920, 9.4; 2-CF3C5H4N, picolinic acid, 53, 139-40¡ã, 1.4166, -; 3-CF3C5H4N, nicotinic acid, 25, 113-15¡ã, 1.4150, -; 4-CF3C5H4N, isonicotinic acid, 57, 108-10¡ã, 1.4155, -; 2-(trifluoromethyl)quinoline, quinaldic acid, 72, 233¡ã (m. 61.5-2.5¡ã), -, -; 4,5-bis(trifluoromethyl)imidazole, 4,5-imidazoledicarboxylic acid, 80, -(m. 167.5-8.0¡ã), -, -.
Journal of Organic Chemistry published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C3H6F3N, Name: 1,1,1-Trifluoropropan-2-amine.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia