In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C20H23FN2O2
R-enriched cyanodiol (lOg, 0.029 moles) was dissolved in MDC (30ml) at 20-40 C. To the obtained clear reaction mass imidazole (5.96g, 0.0438 moles) followed by a solution of t-butyldimethylsilylchloride (TBDMSC1) (6.60g, 0.04 moles) in dichloromethane (10ml) was added at 20-40 C and the reaction mass stirred further at 20-30C for 1-2 hours. Then the reaction mass was directly washed with water (30ml x 3) after which the lower organic layer was separated and concentrated under vacuum at 35-40 C which yielded l l .Ogm title compound ( lib) as a off white solid. 1H-NMR in DMSO at 300MHz (ppm):0.23-0.24 (d,3H), 0.17-0.18(d,3H), 0.76- 0.77 (s, 9H), 0.83-0.85 (d, lH), 1.17-1.22 (m,lH), 1.41-1.45 (m,lH), 2.03 (s,6H), 2.08-2.25 (m,4H), 4.27-4.33 (dd,lH), 4.74-4.79 (dd,lH), 7.07-7.13 (t,2H), 7.23- 7.27 (m,2H),7.80-7.83 (d,3H) FT-IR as such (cm”1): 2952, 2855, 2227, 1599, 1506, 1470, 1253, 1216, 1160, 1122, 1109, 1092, 1035, 1016, 958, 897 Mass Analysis (ESI, +ve mode): Molecular ion peak observed at 457.47 a.m.u which corresponds to (M+H)+ peak of title compound DSC Analysis: Two Endotherm peaks observed at 124.89 and 136.30 C XRPD Analysis (Observed 2Theta values):8.09, 9.32, 10.45, 11.44, 12.34, 13.29, 14.02, 15.57, 16.26, 16.87, 17.51, 18.18, 18.71, 19.34, 19.87, 20.39, 20.99, 21.47, 22.13, 22.49, 23.01, 23.29, 24.49, 24.87, 25.33, 25.74, 26.29, 26.78, 27.03, 27.52, 28.26, 28.69, 29.05, 29.41, 29.61, 30.13, 31.44, 32.09, 32.37, 32.86, 33.17, 33.77, 34.78, 35.16, 35.81, 36.74, 37.54, 38.33, 38.64, 39.45, 40.16, 41.24, 41.59, 42.24, 43.03, 44.29, 45.79, 47.81, 48.49 Purity by HPLC : 91 27%
The synthetic route of 103146-25-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; IPCA LABORATORIES LIMITED; REGURI, Buchi Reddy; PRASAD, Ashok; RAWAT, Ajay Singh; RAJPUT, Sandip; SANTAN, Rohit B; (36 pag.)WO2017/9866; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts