HCID 12362579, compound → 3-Phenyl-3H-spiro[2-benzofuran-1,4'-piperidin]-1'-amine

Participants

Reaction Steps

A solution of 7.1 g of 1'-nitroso-1,3-dihydro-3-phenylspiro[isobenzofuran-1,4'-piperidine], Example 1, in 75 ml of glacial acetic is added to a stirring suspension pf 7.1 g of zinc dust in 50 ml of glacial acetic acid and 50 ml of water while maintaining the reaction temperature between 10° and 20° C. The reaction mixture is stirred for 15 minutes at ambient temperature and then at 80° C. for 5 minutes; an additional 4.7 g of zinc dust are introduced and stirring is continued for an additional 10 minutes. The heated mixture is filtered, the precipitate is washed with hot 1N hydrochloric acid and the combined filtrate and washings are basified and extracted with chloroform. The organic solution is dried and the solvent is removed, leaving a white crystalline solid, 1'-amino-1,3-dihydro-3-phenylspiro[isobenzofuran-1,4'-piperidine], which is recrystallized from ethanolto to give the pure product, mp 143°-145° C.

Provenance & Evidence