Synthetic Route of 5414-21-1, 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. 5414-21-1, name is 5-Bromovaleronitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
[0526] To a stirred solution of [1-(2-(trimethylsilyl)ethoxymethyl)-(1H-benzimidazol-2-ylmethyl)]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (188 mg, 0.455 mmol) and diisopropylethyl amine (0.26 ml<1.49 mmol) in CH3CN was added 5-bromovaleronitrile (0.12 mL, 1.03 mmol). The mixture was heated at 80 C. for 47 hours, after which time the reaction was cooled to room temperature. After removal of volatiles under reduced pressure, the residue was dissolved in CH2Cl2 (20 mL). The solution was washed with brine (3×15 mL). The aqueous phase was extracted with CH2Cl2 (1×15 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure to give a crude orange oil (306 mg). Purification of this oil by column chromatography (1.75 cm OD, 14 g silica, 40:1 CH2Cl2: CH3OH) afforded the purified tertiary amine (110 mg, 50%). [0527] The amine from above (110 mg) was dissolved in ammonia saturated CH3OH(12 mL) and treated with Raney-Nickel (410 mg). The mixture was shaken on a Parr hydrogenator at 50 psi H2 for 20 hours, after which time the mixture was filtered through celite and concentrated to give a crude yellow-orange oil (124 mg). [0528] The amine from above (124 mg) was dissolved in 4N HCl (2 mL) and heated to 50 C. for 6 hours. The mixture was then cooled to room temperature and basified with 10N NaOH (final pH>13). This aqueous phase was extracted with CH2Cl2 (4×10 mL). The organic phase was then dried (Na2SO4), filtered and concentrated to give a crude brown foam (83 mg). Purification of this foam by radial chromatography on silica gel (40:1:1 CH2Cl2: CH3OH: NH4-OH) afforded the pure freebase (38 mg, 46% over two steps). [0529] Using the General Procedure D: Conversion of the freebase from above (38 mg) to the hydrobromide salt gave COMPOUND 50 as a white solid (53 mg, 76%). 1H NMR (D2O) delta 1.14-1.28 (m, 2H), 1.39-1.57 (m, 4H), 1.77-1.90 (m, 1H), 1.96-2.10 (m, 1H), 2.13-2.23 (m, 1H), 2.31-241 (m, 1H), 2.46-2.57 (m, 1H), 2.73-2.90 (m, 3H), 2.96-3.03 (m, 2H), 4.38 (d, 1H, J=16.7 Hz), 4.47-4.57 (m, 2H), 7.60 (dd, 2H, J 6.3, 3.3 Hz), 7.80 (dd, 2H, J=6.2, 3.1 Hz), 7.86 (dd, 11H, J=7.9, 6.0 Hz), 8.31 (d, 1H, J=7.0 Hz), 8.62 (d, 1H, J=4.7 Hz). 13C NMR (D2O) delta 20.40, 23.88, 26.92, 27.63, 27.87, 39.68, 48.51, 52.09, 60.86, 114.26 (2 carbons), 125.85, 126.83 (2 carbons), 131.17, 139.29, 140.47, 147.92 (2 carbons), 151.48, 152.00. ES-MS m/z 364 (M+H) Anal Calc. for C22H29N5 3.1HBr 2.6H2O: C, 39.97; H, 5.69; N, 10.59; Br, 37.46. Found: C, 39.96; H, 5.64; N, 10.62; Br, 37.36.
The synthetic route of 5-Bromovaleronitrile has been constantly updated, and we look forward to future research findings.