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P., Seto, C. T., Simanek, E. E., and Whitesides, G. M. (1994). J. Am. Chem. Soc., 116, 1725\u20131736.","DOI":"10.1021\/ja00084a013"},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Hiroi, K., and Abe, J. (1991). Chem. Pharm. Bull., 39, 616\u2013621.","DOI":"10.1248\/cpb.39.616"},{"key":"ref_28","unstructured":"Triethylamine was used instead of diisopropylethylamine."},{"key":"ref_29","unstructured":"Preparation of 2-imidazol-1-yl-ethanethiol (l): To a reflux solution of imidazole (9.002 g, 132.2 mmol) in anhydrous toluene (120 mL) was added a solution of ethylene sulfide (2.6 mL, 44.0 mmol) in anhydrous toluene (50 mL) during 21 hr and was refluxed for more 2 hr. The solvent was evaporated in vacuo and the residue was diluted with diethyl ether (50 mL) and cooled to -6 \u00b0C (formation of solid). The mixture was filtered, washed the solid with Et2O (20 mL) and the combined liquid fractions were evaporated to dryness and purified by distillation; b.p. 90 - 94 \u00b0C\/ 0.04 mmHg, to give 7.381 g of a 1.3:1.0 mixture (by 1H-NMR) of 2-imidazol-1-yl-ethanethiol (l) and imidazole as a clear colourless oil; \u03bdmax (film)\/cm\u22121 3110, 3037, 2940, 2840, 2701, 2616, 1509, 1446, 1327, 1293, 1225, 1111, 1072, 1066, 929, 907, 827, 748, 663; \u03b4H (400 MHz; CDCl3) 1.36 (1H, br s, SH), 2.87 (2H, t J 6.6, CH2S), 4.15 (2H, t J 6.6), 6.96 (1H, s), 7.11 (1H, s), 7.55 (1H, s); m\/z (EI) 128 (M+), 101, 81, 69, 61; HRMS calcd. for C5H8N2S: 128.0408, found: 128.0410."},{"key":"ref_30","unstructured":"Ethyl 11-aminoundecanoate [31] (1 eq), triethylamine (1 eq) in 1,2-dichloroethane (reflux, 24 hr) was used."},{"key":"ref_31","unstructured":"Preparation of ethyl 11-aminoundecanoate (y): To a suspension of 11-aminoundecanoic acid (0,017 mol, 3.5g ) in absolute ethanol (60 mL) was added concentrated sulphuric acid (0.020 mol, 1.12 mL). The resulting white solution was heated at reflux overnight, cooled 0\u00b0C and neutralized with aqueous saturated bicarbonate solution. The precipitated product was then collected by filtration, washed with cold water, and recrystallized from aqueous ethanol to give ethyl 11- aminoundecanoate (y, 2.4g, 58 %), m. p. 65 \u00b0C; \u03bdmax (NaCl)\/cm\u22121; 3332, 2924, 2854, 1736, 1566, 1473, 1180; \u03b4H (400 MHz; DMSO-d6) 1.15 (3H, t, J= 7.1 CO2CH2CH3), 1.22 (12H, s, NH2CH2CH2(CH2)6CH2CH2CO2Et), 1.31 (2H, br, CH2CH2CO2Et), 1.48 (2H, br, NH2CH2CH2), 2.24 (2H, br, CH2CO2Et), 2.86 (2H, d, J= 4.04, NH2CH2), 4.02 (2H, q, J= 7.1, -COOCH2CH3); \u03b4H (400 MHz; CDCl3) 1.20-1.24 (15H, m, NH2CH2CH2(CH2)6CH2CH2CO2CH2CH3), 1.45 (2H, br, CH2CH2CO2Et), 1.58 (2H, br, NH2CH2CH2), 2.25 (2H, t, J= 8, CH2CO2Et), 2.67 (2H, t, J= 8, NH2CH2), 4.09 (2H, q, J= 8, CO2CH2CH3); \u03b4C (CDCl3) 14.18, 24.90, 26.77, 29.06, 29.17, 29.31, 29.44, 34.30, 41.34, 60.05, 173.78; m\/z (CI) 230 (MH+), 228, 184 ; EIMS calcd. for C13H28NO2: 230.211, found: 230.212."},{"key":"ref_32","unstructured":"In the case of the preparation of 1,3,5-triazines containing the dimethylamino group dimethylammonium chloride (1.0 mol eq.) and diisopropylethylamine (3.2 mol eq.) were used."},{"key":"ref_33","unstructured":"Preparation of (2-methoxyethyl)methylamine (j): A stirred solution of anhydrous triethylamine (5.0 mL, 53.63 mmol), 2-(methylamino)ethanol (4.028 g, 53.63 mmol), tetrabutylammonium bromide (432 mg, 1.34 mmol) and benzyl chloride (4.1 mL, 53.63 mmol) in anhydrous benzene (40 mL) was refluxed for 2 days under argon. The mixture was partitioned between Et2O (70 mL) and aqueous sodium carbonate (50 mL). The aqueous phase was extracted with diethyl ether (2 x 70 mL), the combined organic layers were dried (MgSO4), filtered, evaporated to dryness and purified by distillation; b.p. 86 - 90 \u00b0C\/0.05 mmHg, to give 2-(benzylmethylamino)ethanol (e, 4.654 g, 79 %) as an colorless liquid; \u03bdmax (film)\/cm\u22121 3406 (OH), 3099, 3076, 3042, 2957, 2889, 2855, 2804, 1503, 1458, 1372, 1077, 1032, 742, 702; \u03b4H (400 MHz; CDCl3) 2.22 (3H, s, NMe), 2.59 (2H, t J 5.2, 2-H), 2.86 (1H, br s, OH), 3.56 (2H, s, CH2Ph), 3.62 (2H, t J 5.2, 1-H), 7.28- 7.34 (5H, m, Ph); m\/z (FAB) 166 (MH+), 134, 120, 107; HRMS calcd. for C10H16NO: 166.1232, found: 166.1240. To a solution of the above amino-alcohol (1.364 g, 8.25 mmol) in anhydrous THF (60 mL) at room temperature under argon was added sodium hydride (396 mg, 50 % oil dispersion, 8.25 mmol). After 15 hr was added iodomethane (0.51 ml, 8.25 mmol), stirred for 8 hr and refluxed for 1.5 hr. The mixture was partitioned between Et2O (50 mL) and saturated aqueous ammonium chloride (70 mL). The aqueous phase was extracted with Et2O (2 x 70 mL), the combined organic layers were dried (MgSO4), filtered, evaporated to dryness and chromatographed on a silica gel column (1:0 to 6:4 hexane\/ethyl acetate) to afford benzyl-(2- methoxyethyl)methylamine (1.159 g, 78 %) as a slightly yellow liquid; \u03bdmax (film)\/cm\u22121 3076, 3042, 2985, 2940, 2883, 2849, 2815, 2798, 1503, 1458, 1372, 1123, 1077, 1054, 742, 702; \u03b4H (400 MHz; CDCl3) 2.26 (3H, s, NMe), 2.60 (2H, t J 5.8, 2-H), 3.34 (3H, s, OMe), 3.51 (2H, t J 5.8, 2-H), 3.55 (2H, s, CH2Ph), 7.26-7.32 (5H, m, Ph); m\/z (FAB) 180 (MH+), 166, 154, 138, 134, 120; HRMS calcd. for C11H18NO: 180.1388, found: 180.1380. A mixture of the above compound (198.9 mg, 1.11 mmol) and Pd\/C (10 %) (73 mg) in ethanol (6 mL) under hydrogen atmosphere (balloon) was strongly stirred at room temperature during 1.5 hr (complete reaction by TLC). Argon atmosphere was introduced and the mixture was used directly to the next step."},{"key":"ref_34","unstructured":"In the other examples, pure amines were added to the reaction mixture."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/11\/1\/81\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T22:24:39Z","timestamp":1760221479000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/11\/1\/81"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006,1,31]]},"references-count":79,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2006,1]]}},"alternative-id":["11010081"],"URL":"https:\/\/doi.org\/10.3390\/11010081","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2006,1,31]]}}}