Electric Literature of 90390-33-3,Some common heterocyclic compound, 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, molecular formula is C7H7ClFN, 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.
A solution of 3-hydroxy-2-oxo-1-phenylpiperidine-3-carboxylic acid (80 mg) and 3-chloro-5-fluorobenzylamine (65 mg) in dichloromethane (15 ml) is stirred with triethylamine (0.14 ml) and propanephosphoric anhydride (T3P; 0.33 g) firstly at 0 C., then at RT for 1 h under nitrogen. When the reaction is complete, the mixture is diluted with dichloromethane and washed with 10% sodium bicarbonate solution and saturated NaCl solution. Filtration, evaporation and chromatography gives the product as colourless solid with a yield of 12% (15 mg); 10307] LCMS: mass found (M+1,377.0)10308] Method: A-0. 1% ofTFA in H20, B-O. 1% of TFA in ACN: flow-2.0 ml/min.10309] Column: X Bridge C8 (50×4.6 mm.3.5p)+ve mode10310] Rt (mm): 4.03 area % 92.24 (max), 91.79 (220 nm)10311] HPLC:10312] Method: A: 0.1% of TFA in H20, B: 0.1% ofTFA in ACN, flow rate:2.0 ml/min10313] COLUMN: XBridge C8 (50×4.6) mm, 3.5 tm10314] Rt (mm): 4.01 area % 94.30 (max), 94.44 (220 nm);
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-5-fluorobenzylamine, its application will become more common.
Reference:
Patent; MERCK PATENT GmbH; Heinrich, Timo; Zenke, Frank; Krier, Mireille; Friese-Hamim, Manja; Seenisamy, Jeyaprakashnarayanan; US2015/31670; (2015); A1;,
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