[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([NH2:21])[CH2:19][NH2:20].[Li].[H-]>O>[C:2]1([CH:1]2[C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[CH2:11][NH:21][CH2:18][CH2:19][NH:20]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Add 40 g. of the condensation product of o-benzoylbenzoic acid and ethylenediamine in small portions to a suspension of 15 g. of lithium aliminum hydride in 1500 ml. of anhydrous either with stirring. Reflux with stirring for 16 hours. Cool and add water carefully to decompose excess hydride. Separate the ether layer, dry over magnesium sulfate, and remove the solvent under reduced pressure to obtain 1,2,3,4,5,6-hexahydro-1-phenyl-2,5-benzodiazocine, m.p. 125° C. To prepare the dihydrochloride, dissolve the base in anhydrous ether and saturate with dry hydrogen chloride. Separate the precipitated solid, and recrystallize from ethanol to obtain 1,2,3,4,5,6-hexahydro-1-phenyl-2,5-benzodiazocine dihydrochloride, m.p. 297° C. (dec.).
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