Fenpiprane

Scheme 15.12 Synthesis of fenpiprane using hydroaminomethylation of diphenylethene.

Silicon Containing Derivatives of the Antihistamines Diphenhydramine and Fenpiprane... 

The formation of distonic superelectrophile 104 provides a high-yield route to the antispasmodic dmg, fenpiprane 105. The 1,4-dication (108), 1,5-dication (106) and 1,6-dication (107) have likewise been shown to react with benzene in high yields.39 The superelectrophilic vinyl-dications (109-110) have also been studied.40,41... 

Acepromazine, acetophenazine, adiphenine, azacyclonol, barban, benzilonium, benzyl nicotinate, biperiden, clemastine, clomiphene, cyclothiazide, dextropropoxyphene, dichlorprop, dicophane, diperodon, diphem-anil, diphenidol, emepronium, etenzamide, fenpiprane, flurbiprofen, haloperidol, mepenzolate, methyl-piperidyl benzilate, mexiletine, nadolol, penfluridol, phenaglycodol, phenylbutazone (100°), phosalone, pimozide, pipazethate (100°— red), pipoxolan, pyrrobutamine, rotenone, sotalol (100°), sulindac, veratrine, zimeldine... 

Acepromazine (- red), adiphenine (-> blue), benorylate, bephenium hydroxynaphthoate, bibenzonium, buclosamide (blue rim), bunamidine, chlorpromazine (-> violet), clefamide (— brown), codeine, colchicine, cyclazocine, cyclomethycaine (— brown), debrisoquine, diaveridine, dibenzepin, diethazine (— violet with excess reagent), diethylthiambutene (-> green-blue), dimethindene, dimethoxanate (— brown), dimoxyline, dipipanone (— blue), dothiepin, doxorubicin, doxycycline (-> yellow), ethopropazine violet), fenpiprane,... 

Fenpiprane Hydrochloride 218-219d Solanidine 228-232 Thiopropazate Hydrochloride... 

Reductive amination of aldehydes prepared from hydrofonnylation is a useful route to amines. Botteghi, et al. reported the synthesis of racemic Tolterodine by sequential hydroformylation-reductive amination [18]. Hydroaminomethylation (tandem hydroformylation/reductive amination) has recently been used to prepare a wide variety of pharmaceutical compounds [19]. Representative examples are shown in Fig. 5. Hydroaminomethylation of 1,1-diarylethenes leads to l-(3, 3-diaiylpropyl)amines, such as fenpiprane [20, 21]. Heterocyclic aUyUc amines undergo hydroaminomethylation to form pharmaceutically active diamines, such as etymemazine [22]. Ibutilide and fexofenadine have been prepared by hydroamino-methylatiOTi of 1-aiylallyl alcohols in the presence of the requisite amines [23,24]. Although none of these reactirais has been developed into a commercial process, the widespread utility of the hydroaminomethylation reaction makes it likely that it will be used commercially... 

---