Verfahren zur Herstellung eines 1-substituierten 3-Phenoxypyrrolidins

1289867 3-Phenoxypyrrolidine derivatives A H ROBINS CO Inc 19 Dec 1969 [23 Dec 1968] 61968/69 Heading C2C The invention comprises compounds of formula and their acid addition salts, wherein R is C 1-8 alkyl or alkoxy, C 2-8 alkenyl or alkynyl, or carbamoyl, carbamoyloxy, phenoxy, benzoyloxy, α-hydroxybenzyl, styryl, hydroxy, 1,2-dihydroxyethyl, amidino or carbalkoxy, or (when n is 0) phenyl, the phenyl groups in any of these radicals being optionally substituted, R1 and R2 are each H, C 1-8 alkyl or alkoxy, or CF 3 , Ac, F, Cl or Br, and n is 0-4. These compounds are prepared by reacting (a) the corresponding N-unsubstituted 3- phenoxypyrrolidines (I) with R-(CH 2 ) n -X, where X is halogen; (b) I or the N-hydroxyalkylphenoxypyrrolidines with nitrourea, or the appropriate isocyanates or carbamoyl halides, or S-methylisothiourea ; or (c) the corresponding N-benzyl 3-phenoxypyrrolidines (II) with CNBr followed by hydrolysis of the N-cyano derivative to give the N-carbamoyl compounds (III). I are prepared by hydrogenolysis of II, except when R1 and/or R2 is halogen, when hydrolysis of III is preferred. Therapeutic compositions for oral or parenteral administration comprise compounds of the above formulµ, which have a pharmacological action on the central nervous system, and in particular are tranquillizers, muscle relaxants and anticonvulsants.