camazepam
camazepam Basic information
- Product Name:
- camazepam
- Synonyms:
-
- Albego
- B-5333
- Dimethylcarbamic acid 7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl ester
- KTH-497
- SB-5833
- dl-CaMazepaM
- N,N-DiMethylcarbaMic Acid 7-Chloro-2,3-dihydro-1-Methyl-2-oxo-5-phenyl- 1H-1,4-benzodiazepin-3-yl Ester
- RaceMic CaMazepaM
- CAS:
- 36104-80-0
- MF:
- C19H18ClN3O3
- MW:
- 371.82
- EINECS:
- 252-866-6
- Product Categories:
-
- Aromatics
- Heterocycles
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Mol File:
- 36104-80-0.mol
camazepam Chemical Properties
- Melting point:
- 173-174°
- Boiling point:
- 568.3±50.0 °C(Predicted)
- Density
- 1.2902 (rough estimate)
- refractive index
- 1.6470 (estimate)
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 2.21±0.50(Predicted)
- color
- White to Off-White
- Stability:
- Light Sensitive
camazepam Usage And Synthesis
Originator
Albego,Simes,Italy,1977
Uses
Anxiolytic. Controlled substance (depressant).
Definition
ChEBI: Camazepam is a benzodiazepine.
Manufacturing Process
A suspension of 100 g of 7-chloro-5-phenyl-1-methyl-3-hydroxy-1,3-dihydro-
2H-1,4-benzodiazepin-2-one in 700 ml of anhydrous pyridine, kept stirred
between 0°C and +5°C, is slowly treated, during 20 to 30 minutes, with 54.5
ml phenyl chlorocarbonate. The temperature is gradually allowed to rise to
20°-25°C and stirring is maintained at this temperature during 24 hours.
2 l of water are then slowly added (during about 30 minutes) and stirring is
maintained during 1 hour. The precipitate which has been formed is collected
on a filter, washed thoroughly with water, dried in a vacuo at 50°C and
recrystallized by dissolving it at 60°C in 1,400 ml dioxane, the solution thus obtained being evaporated under reduced pressures to one-half of its volume,
and 1,700 ml of ligroin (BP 80°C to 120°C) being added thereto.
7-chloro-5-phenyl-1-methyl-3-phenoxycarbonyloxy-1,3-dihydro-2H-1,4-
benzodiazepin-2-one is thus obtained, with a melting point of 162°C to 164°C.
A suspension of 45 g 3-phenoxycarbonyloxy-1-methyl-7-chloro-5-phenyl-1,3-
dihydro-2H-1,4benzodiazepin-2-one in 450 ml methanol is treated with
stirring, with 43 ml of a solution of dimethylamine in methanol (containing 31
g dimethylamine in 100 ml). Stirring is maintained at 20°C to 25°C during 5
hours. The reaction mixture is filtered, and the filtrate is diluted with 450 ml
water. The precipitate thus formed, is 3-(N,N-dimethylcarbamoyloxy)-1-
methyl-7-chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one, which is
collected on a filter, dried and recrystallized from ethyl acetate, and has a
melting point of 173°C to 174°C.
Therapeutic Function
Anxiolytic