1-Indanone → Piperidine

Participants

Reaction Steps

Synthesis substrates 5H-indeno[1,2-b]pyridin-5-one and 5H-indeno[1,2-b]pyridine (as 4-azafluorene from Aldrich Chemical, Inc.) and their derivatives are prepared according to a general procedure of Parcell and Hauck, J. Org. Chem., 21, 3468 (1963), wherein the piperidineenamine of 2,3-dihydro-1H-inden-1-one (available from Aldrich Chemical, Inc.) --4,--5 or --6-chloro or fluoro-2,3-dihydro-1H-inden-1-one (Oliver and Marechal, Bull. Soc. Chim. France, (1973), 3092), 6-chloro-5-cyclopentylmethyl-2,3-dihydro-1H-inden-1-one (Biere et al., Eur. J. Med., 18, 255 (1983), 5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (Koo, J. Amer. Chem. Soc., 75, 1891 (1953)), 5 or 6-methoxy-2,3-dihydro-1H-inden-1-one (available from Aldrich Chemical, Inc.,) or other substituted 1-indanones is formed from piperidine in the presence of p-toluenesulfonic acid catalyst according to the procedure of Heyl and Herr, J. Amer. Chem. Soc., 75, 1918 (1953). The resulting piperidineenamine is reacted with 3-bromopropylamine hydrobromide or hydrochloride (available from Aldrich Chemical, Inc.) to yield an imine product.

Provenance & Evidence