Diphenylacetonitrile is an organic compound with the formula . A colorless solid, it is widely used in the pharmaceutical industry.
Synthesis In Hoch's original procedure, phenylacetonitrile was halogenated with molecular bromine to give bromobenzyl cyanide (BBC). This species was then reacted with benzene in the presence of aluminium trichloride to afford diphenylacetonitrile. This procedure has been optimized over the years.
An alternative route involves the reaction of bromodiphenylmethane with sodium cyanide under phase transfer conditions:
Applications Opioid analgesics: Bezitramide, Dipipanone, Dipyanone, Isomethadol, LAAM, Methadone,https://bbgate.com/threads/synthesis-of-methadone.193/ Noracymethadol, Normethadone, Norpipanone, Piritramide, R-4066, R 4837 [59708-47-3], R-5260 [1109-69-9] (25ii): Psychostimulants: 2-Benzhydrylpiperazine [28217-87-0],Jongh David Karel De, Akkerman Antonie Marie, Kofman Hendrik,& Vries George De, US2997473 (1961 to Nederlandsche Combinatie voor Chemische Industrie NV).Karel De Jongh David, et al. GB893391 (1962 to Nederlandsche Combinatie voor Chemische Industrie NV). Desoxypipradrol, DPA-1 [3139-55-7], β-Phenylmethamphetamine, Desoxyhexapradol. Antidepressants: McN-4187, McN 4612-z (Parent compound to JNJ-7925476, McN 5707 & McN5652, etc. SAR with tametraline) & deschloro-clemeprol (although the literature procedure for 1,1-diphenylacetone is different to this). Antipsychotics: McN-4171 This agent is an analog of butaclamol. McN-4612-Y is also described in the attached article. This is similar to McN 4612-z, which was described above except it is the opposite optical antipode. It is also possible to make PC12515636 from the primary amine using a double Michael reaction followed by Dieckman condensation, which is the standard method of 4-piperidone synthesis. Antispasmodics: Aminopentamide, Buzepide, Fenpiverinium, Fenpipramide Urinary incontinence: Darifenacin, Imidafenacin Anti-diarrhoeals: Difenoxin, Diphenoxylate, Nufenoxole Choleretic and spasmolytic agent: Diisopromine Analeptic (respiratory stimulant): Doxapram Antiarrhythmic: IsopropanamideJanssen Paul Adriaan Jan & Jongh David Karel De, US2884436 (1959 to Nederlandsche Combinatie voor Chemische Industrie NV). Cytochromes P450 inhibitor: Proadifen 2,2-DEP [36794-51-1] (Hamilton Morris's diphenidine positional isomer drug).
See also Hoch also discovered the Hoch-Campbell ethylenimine synthesis. Diphenylacetic acid
References