DERIVATE DES L-PHENOXY-3-AMINO-PROPAN- 2-OLS UND VERFAHREN ZU IHRER HERSTELLUNG

1443135 Phenoxypropanolamines CASSELLA FARBWERKE MAINKUR AG 19 Dec 1974 [27 Dec 1973] 54911/74 Heading C2C [Also in Division A5] Compounds of the general Formula I (X =-CR 1 =CHCOAr, -CHR 1 CH 2 CH(OH)Ar; R 1 =H, Me; Ar=aromatic or quasi-aromatic 5- or 6-membered monocyclic ring linked through a carbon atom and having one or two N, O and/or S atoms and optionally substituted by one or more methyl groups; A = alkoxymethyl, alkoxyalkoxy, hydroxyalkoxy, NHCONR 2 R 3 ; R 2 , 3 = H, alkyl, alkenyl, cycloalkyl or NR 2 R 3 = saturated 5- or 6-membered monocyclic ring optionally having an O or S atom), their aldehyde condensation products and acid addition salts are prepared by (a) reacting the corresponding phenoxypropanolamine with XY (Y halogen or (X=-CR 1 =COHCOAr)OH, OK, ONa), (b) reacting a corresponding 3-phenoxy-2-hydroxypropyl halide and/or phenoxymethyloxirane with XNH 2 , (c) reacting the corresponding phenol with XNHCH 2 Z (Z=oxiranyl and/or 2-halo-1-hydroxyethyl), (d) reducing a product in which X=-CR 1 =CHCOAr or the corresponding compound in which the CHOH group is replaced by CO, (e) reducing the'compound corresponding to a product in which X= -CHR 1 CH 2 CH(OH)Ar but in which the other CHOH group is replaced by CO or (f) reducing a compound of Formula I but in which or the corresponding compound in which the CHOH group is replaced by CO, optionally followed by conversion to an oxazolidine by condensation with R 4 CHO (R 4 =H, C 1-4 alkyl) or salt formation. The preparation of starting materials for processes (a), (b) and (c) and benzyl derivatives of certain of the phenols and amines (XNH 2 ) is described.