| Identification | Back Directory | [Name]
6-allyl-6,7-dihydro-5H-dibenz[c,e]azepine | [CAS]
146-36-1 | [Synonyms]
Ilidar base
6-allyl-6,7-dihydro-5H-dibenz[c,e]azepine
6,7-Dihydro-6-(2-propenyl)-5H-dibenz[c,e]azepine
5H-Dibenz[c,e]azepine, 6,7-dihydro-6-(2-propen-1-yl)- | [EINECS(EC#)]
205-667-3 | [Molecular Formula]
C17H17N | [MDL Number]
MFCD01731332 | [MOL File]
146-36-1.mol | [Molecular Weight]
235.32 |
| Hazard Information | Back Directory | [Originator]
Ilidar,Roche,US,1954 | [Definition]
ChEBI: Azapetine is a benzazepine. | [Manufacturing Process]
29 grams of diphenic acid were stirred in 900 cc of acetic anhydride at 120°C
for one hour, The cooled mixture was filtered and washed with acetic acid to
give diphenic anhydride, colorless crystals, MP about 222-226°C.
24.11 grams of diphenic anhydride were mixed with 50 cc of concentrated
ammonia. The mixture warmed up and cooling was applied, after which the
mixture was stirred until a clear solution formed and for 1? hours afterward.
The mixture was acidified and allowed to stand overnight. Water was added,
initiating precipitation. The mixture was chilled and filtered to yield
diphenamic acid, a colorless solid, MP about 191-193°C.
23.5 grams of diphenamic acid were heated at 200°C in an oil bath, first for
about 20 hours at atmospheric pressure and then for about 10 hours at about
20 mm.
Melting points were taken at intervals in order to gain an idea of the extent of
reaction. The final residue was boiled with alcohol but since the solid exhibited
insufficient solubility in the hot solvent, the mixture was filtered. The residue
consisted of tan crystals, MP about 220-221°C, and the filtrate on cooling
gave an additional crop of tan crystals, MP about 219-221°C. The two
materials were identical and consisted of diphenimide.
5.58 g of diphenimide were placed in a Soxhlet thimble and extracted for
about 3 days with a boiling mixture of 9.0 g of lithium aluminum hydride in
600 cc of sodium-dried ether. Excess lithium aluminum hydride was then
decomposed cautiously with water and the mixture was filtered through a
filter aid by suction. The filtrate consisted of two layers. The ether layer was
separated and dried with anhydrous potassium carbonate and acidified with
alcoholic hydrochloric acid to give 6,7-dihydro-5H-dibenz[c,e]azephine
hydrochloride, MP about 287-289°C.
One gram of 6,7-dihydro-5H-dibenz[c,e]azepine hydrochloride was dissolved
in water, made alkaline with concentrated ammonia, and the resultant base
extracted twice with benzene, The benzene layers were combined, dried with
anhydrous potassium carbonate, and mixed with 0.261 g of allyl bromide at
25-30°C. The reaction solution became turbid within a few minutes and
showed a considerable crystalline deposit after standing 3? days. The mixture
was warmed 1 3/4 hours on the steam bath in a loosely-stoppered flask, then
cooled and filtered. The filtrate was washed twice with water and the benzene
layer evaporated at diminished pressure. The liquid residue was dissolved in
alcohol, shaken with charcoal and filtered. Addition to the filtrate of 0.3 gram
of 85% phosphoric acid in alcohol gave a clear solution which, when seeded
and rubbed, yielded 6-allyl-6,7-dihydro-5H-dibenz[c,e]azepine phosphate, MP
about 211-215°C with decomposition. | [Therapeutic Function]
Adrenergic blocker | [Safety Profile]
Poison by intraperitoneal andintravenous routes. Moderately toxic by ingestion,subcutaneous, and intramuscular routes. When heated todecomposition it emits toxic fumes of NOx. |
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