Proxazole Citrate

Preparation of 3-(N-Formyl-N-Methyl)-Aminopropanol-1 A mixture of 40 grams of 3-methylaminopropanol-1 and 20 grams of formamide Is heated while stirring for 4 hours at 165°C. The crude product is fractionated in vacuo using a Widmer column yielding substantially pure 3-(N-formyl-N-methyl)-aminoprOpanol-1. 

Preparation of 5-[3-(N-Formyl-N-Methyl)-Aminopropyl]-SH-Dibenzo[a,d] Cycloheptene  

To a suspension of 3.9 grams of potassium amide is slowly added a solution of 19.2 grams (0.1 mol) Of 5H-dibenzo[a,d] cycloheptene in 600 ml of ether with stirring. The suspension is refluxed with stirring for 3 hours, then cooled to room temperature and a solution of 0.1 mol of 3-(N-formyl-N-methyl)-aminopropyl chloride in 100 ml of ether added. The mixture is then refluxed with stirring for 5 hours and then 100 ml of water added. The ether layer is then washed with dilute hydrochloric acid, then water and then dried over magnesium sulfate and evaporated to dryness yielding 5-[3-(N-formyl-N-methyl)-amino-propyl] -5H-dibenzo[a,d] cycloheptene. 

Preparation of 5-(3-Methylaminopropyl)-5H-Dibenzo[a,d]Cycloheptene from 5-[3-(N-Formyl-N-Methylj-Aminopropyl]SH-Dibenzo[a/i]Cycloheptene 29.5 grams of 5-[3-(N-formyl-N-methyD-aminoprOpyl] -5H-dibenzo[a,d] cycloheptene is refluxed for 24 hours under nitrogen in a solution of 36.3 grams of potassium hydroxide in 378 ml of n-butanol. After cooling to room temperature, the solvent Is evaporated in vacuo, the residue is stirred with 200 ml of water, 300 ml of n-hexane, the layers separated, the water layer extracted with 100 ml of n-hexane and the combined hexane layers washed with water (2 x 100 ml) and then with 

5 N sulfuric acid (100, 80,80 ml). The acid solution Is then alkalized and extracted with ether (2 x 150 mi and 1 x 100 ml), dried over MgS04 and the solution evaporated to dryness yielding substantially pure 5-(3-methylaminopropyl)-5H-dibenzo[a,d]cycloheptene according to U.S. Patent 3,244,748. 

To a suspension of 3.9 grams of potassium amide is slowly added a solution of 19.2 grams (0.1 mol) of 5H-dibenzo[a,d] cycloheptene in 600 ml of ether with stirring. The suspension is refluxed with stirring for 3 hours, then cooled to room temperature and a solution of 

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Butamirate citrate Choline dihydrogen citrate Clomiphone dihydrogen citrate Orphenadrine citrate Perisoxal citrate Proxazole citrate Copper (powder)... 

Hydrocortamate HCI Lidocaine Oxeladin Proxazole citrate Rociverine Tilidine HCI T rapidil... 

Ethyl benzamidoxime Proxazole citrate Ethyl benzilate... 

Sodasone - Prednisolone phosphate sodium Sodelut G Medroxyprogesterone acetate Sodium Cephalotin - Cephalothin sodium Sodiuretic Bendroflumethiazide Sofalead Diphenidol Sofarin - Diclofenac sodium Sofmin Methotrimeprazine Sofro - Pemoline Solacen -Tybamate Solacil Proxazole citrate Solantal - Tiaramide Solantyi - Phenytoin Solaquin - Hydroquinone Solaskil Levamisole HCi I Solatene - /3-Carotene Solatran Ketazolam Solaxin - Chlorzoxazone Solazine - Trifluoperazine Solbrine - Dimenhydrinate Solcillin-C - Cloxacillin Solco H Hydroxocobalamin Soldactone - Canremoate potassium... 

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