Originator
Equilibrin,Nattermann,W. Germany,1980
Manufacturing Process
31.3 g (0.1 mol) of 3-(3'-dimethylaminopropylidene)dibenzo[a,d]cyclohepta-
1,4-diene hydrochloride are dissolved in water, and the free base is liberated
by means of a 28% aqueous solution of sodium hydroxide. The free base is
sucked off, washed with water, and dissolved in 100 ml of methanol. To the
solution are added 31 ml of 30% hydrogen peroxide. After 7 days, the
reaction mixture is diluted with 200 ml of water, and the major part of the
methanol is evaporated in vacuum. The precipitated N-oxide crystals are
filtered off, washed with water, and dried, yielding 27 g of the dihydrate of 3-
(3'-dimethylaminopropylidene)dibenzo[a,d]cyclohepta-1,4-diene N-oxide with
melting point of 102° to 103°C. In dehydrated state the melting point is
228°C to 230°C.
By dissolving the N-oxide in acetone, and bubbling dry hydrogen chlorine gas
through the solution until slightly acid reaction, the hydrochloride of the Noxide
is precipitated as a white crystalline substance with melting point of
172°C to 173.6°C.
The starting material can be prepared in known manner from
dibenzo[a,d]cyclohepta-1,4-diene-5-one by a Grignard reaction with 3-
dimethylaminopropyl magnesium chloride, hydrolysis and dehydration of the
resulting carbinol.
Safety Profile
Poison by ingestion,intraperitoneal, and intravenous routes. An experimentalteratogen. Other experimental reproductive effects. Whenheated to decomposition it emits toxic fumes of NOx.
