Benzhydrylamine

Chemical properties

Colorless liquid

The Uses of Benzhydrylamine

Benzhydrylamine is fine-chemical intermediate used for chiral resolution. It acts as an active pharmaceutical ingredient intermediate. It is also employed as a building block for chemical synthesis. Further, it is used in the preparation of furan-2-carboxylic acid benzhydrylamide by reacting with furan-2-carbonyl chloride.

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 3033, 1986 DOI: 10.1016/S0040-4039(00)84709-7

Synthesis

1) synthesis of diphenylketoxime
After benzophenone 10g, oxammonium hydrochloride 6g, 95% ethanol 20mL are put into reaction flask stirring and dissolving, gradation adds sodium hydrate solid 11g.Finish, reaction solution is heated to 88 DEG C of reaction 2h, then pours in dilute hydrochloric acid solution by reaction solution, occurs white solid, filter to obtain diphenylketoxime 10.7g, yield 99%.
2) synthesis of benzhydrylamine
Diphenylketoxime 0.25g, 95% ethanol 5mL are put into reaction flask, after solution change is clear, adds concentration into 5 × 10 7cFU/mL waxy Bacillus solution 50mL, constant temperature 30 DEG C (rotating speed 200r/min) oscillatory reaction in shaking table.TLC detect without raw material time, add appropriate diatomite in reaction solution and carry out centrifugation, get supernatant liquid acidifying, with dichloromethane extraction, aqueous layer basified and with dichloromethane extraction concentrate to obtain benzhydrylamine 9.0g, yield 91%.

Purification Methods

Crystallise the amine from H2O. The free base absorbs CO2 from the atmosphere; store it accordingly. The hydrochloride M 219.7 m 293-295o, crystallises from H2O. [Beilstein 12 H 1323, 12 IV 3282.]