1-Preparation method of o-chlorophenylethylamine_Kain Industrial Additive

Background and overview^[1]

1-O-chlorophenylethylamine can be used as a pharmaceutical synthesis intermediate. If 1-o-chlorophenylethylamine is inhaled, please move the patient to fresh air; if there is skin contact, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical treatment if you feel uncomfortable; if there is eye contact , you should separate your eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse your mouth immediately, do not induce vomiting, and seek medical attention immediately.

Preparation^[1]

The preparation of 1-o-chlorophenylethylamine is as follows:

(R10=2-chlorophenyl, R1=methyl)

1) In a flask under argon atmosphere, 1,3-dimethylimidazolium iodide 5A (79.6 mg, 0.355 mmol), first silver (41.4 mg oxide, 0.179 mmol), methylene chloride (2.5 mL) was added to the solution and stirred at room temperature for 4 hours. (Pentamethylcyclopentadienyl)iridium(III) diiodide (dimer) (hereinafter referred to as [Cp*IrI2]2) (202.1 mg, 0.174 mmol) was added to the mixture and incubated at room temperature. Join 4. Stir for several hours. After filtration through a glass filter, the filtrate was evaporated to give compound 1a (148.3 mg, 0.219 mmol, 63% yield).

2) Under an argon atmosphere, add compound 1a (4.0mol%) as a catalyst, 28% ammonia water (20mmol), and 1-(o-chlorophenyl)ethanol 3a into a stainless steel sealed container (internal volume 5mL). (1.0 mmol) and stirred at 150°C for 40 hours. After cooling the reaction solution, the contents were transferred to a test tube, and the product 1-o-chlorophenylethylamine was extracted with dichloromethane (15 mL). The crude product obtained by distilling off the solvent was purified by silica gel chromatography (eluent: hexane/ethyl acetate mixed solvent) to obtain 1-o-chlorophenylethylamine 4b (yield 83%).

Main reference materials

[1] WO2016002762 Novel iridium compound, its projection method, a catalyst using the catalyst, and a method for producing a main amine compound using the compound