A very ecofriendly
heterogeneous catalytic method has been used
for the highly selective synthesis of octahydroaminoacridine/1,2,3,4,5,6,7,8-octahydroacridin-9-amine
(OA) by a single-step vapor phase cyclization of cyclohexanone (CHCO)
with a mixture of formamide (HCONH2) and ammonia (NH3) over different nanoporous catalysts, for example, mesoporous
solid acid catalysts, ZnAlMCM-41, AlMCM-41, and ZnMCM-41, and microporous
catalysts, for example, USY, Hβ, HZSM-5, and H-mordenite. In
pharmaceutical companies, the main product, OA, is used as a drug
intermediate in the production of tacrine that is a licensed drug,
which is used for the treatment of Alzheimer’s disease. In
order to determine their catalytic stabilities, recyclable mesoporous
ZnAlMCM-41 catalysts have been reused in this reaction. To find an
optimal parameter for highly selective synthesis of OA, various reaction
parameters have been extensively investigated for this reaction. Additionally,
an important byproduct, 1,2,3,4,5,6,7,8-octahydroacridine, is also
formed by deamination of OA. The mesoporous ZnAlMCM-41(75) produces
92% OA selectivity with 100% CHCO conversion at 0.5 h–1 weight hourly space velocity and 340 °C with
a feed ratio of CHCO/HCONH2/NH3 = 2:1:5.
Interestingly, we have observed from the catalytic results of all
the catalysts used for the single-step selective synthesis of OA that
the ZnAlMCM-41(75) catalyst has higher OA selectivity with exceptional
catalytic activity than other microporous and mesoporous catalysts.