These common heterocyclic compound, 35354-37-1, name is 1-Bromo-5-methylhexane, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: bromides-buliding-blocks
Example 145 (+-)-4-(3-Ethanesulfonylaminophenyl)-trans-3,4-dimethyl-N-(5-methylhexyl)piperidine To a stirred solution of (+-)4-(3-ethanesulfonylaminophenyl)-trans-3,4-dimethylpiperidine (Preparation 39, 120 mg, 0.4 mmol) in N,N-dimethylformamide (7 ml) was added sodium hydrogen carbonate (68 mg, 0.8 mmol) and 1-bromo-5-methylhexane (80 mg, 0.44 mmol). The stirred reaction mixture was heated to 100° C. for 16 h, then allowed to cool. Water (50 ml) was added and the mixture was extracted with diethyl ether (3*50 ml). The combined extracts were washed with brine (50 ml), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica (5 g) column chromatography eluding initially with hexane, then hexane:ethyl acetate:0.880 ammonia (50:50:1) to give a yellow oil (15 mg). The residue was further purified by preparative HPLC on a Phenomenex Magellan.(TM). column, 15 cm*2.1 cm; flow 10.0 ml min-1; employing U.V. detection at 235 nm; eluant acetonitrile:0.1M aqueous ammonium acetate solution:methanol (25:35:40) to afford the title compound as its acetate salt as a yellow oil (10 mg, 6percent). NMR (CDCl3, selected data for the acetate salt): 0.8 (d, 3H), 1.8 (m, 1H), 2.4 (m, 1H), 2.85 (m, 1H), 3.1 (q, 2H), 7.05-7.3 (m, 4H). MS (APCI): M/Z [MH+] 395.2; C22H38N2O2S+H requires 395.3.
The synthetic route of 1-Bromo-5-methylhexane has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Armer, Richard Edward; Dutton, Christopher James; Gethin, David Morris; Gibson, Stephen Paul; Smith, Julian Duncan; Tommasini, Ivan; US2003/78282; (2003); A1;,
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