Benzodiazepine-2-one

Chloro-6-phenyl-1 -methyl-3-hydroxy-1,3-dihydro-2H-1,4-benzodiazepine-2-one... 

A suspension of 45 g 3-phenoxycarbonyloxy-1 -methyl-7-chloro-5-pheny -1,3-dihydro-2H-1,4-benzodiazepin-2-one in 450 ml methanol is treated with stirring, with 43 ml of a solution of dimethylamine in methanol (containlng31 gdimethylamine in 100 ml). Stirring ismaintained 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-methy -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. 

Chemical Name 5-(o-chlorophenyl)-1,3-dihydro-7-nitro-2H-1,4-benzodiazepin-2-one Common Name —... 

A solution of 60 g of chromic anhydride in 40 ml of water was added dropwise to a suspension of 60 g of 2-aminomethyl-1 -methyl-5-chloro-3-(o-fluorophenyl)-indole hydrochloride in 600 ml of acetic acid. The mixture was stirred at room temperature overnight. To the reaction mixture was added 1.1 liters of ether and 1 liter of water and then 800 ml of 28% ammonium hydroxide, in small portions. The ethereal layer separated, washed with water, dried, and concentrated under reduced pressure. The residue (51.8 g) was dissolved in 100 ml of ethanol, and 100 ml of 20% ethanollc hydrogen chloride was added to the solution and the mixture was cooled. The precipitate was collected by filtration to yield 46.5 g of 1 -methyl-7-chloro-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-one hydrochloride, melt-... 

Chemical Name 7-chloro-1-[2-(diethvlamino)ethvl] 5-(o-fluorophenvl)-1,3-dihvdro-2H-1,4-benzodiazepin-2-one... 

To a slightly warm suspension of 3-acetoxy-7-chloro-5-(o-chlorophenyl)-1 3-dihydro-2H-1,4-benzodiazepin-2-one thus obtained was added 4N sodium hydroxide solution with stirring. All the solid dissolved and soon a thick white solid precipitated out. The solid was filtered, washed well with water and recrystallized from ethanol. The product was isolated as a solvate with 1 mol of ethanol. When heated it loses the ethanol of solvation and melts at 166°C to 168 C. 

To a suspension of 3.4 g of 3-acetoxy-7-chloro-1,3-dihydro-5-(o-chlorophenyl)-2H-1,4-benzodiazepin-2-one in 80 ml of alcohol was added 6 ml of 4 N sodium hydroxide. After complete solution had taken place a solid precipitated that redissolved upon the addition of 80 ml of water. The solution was acidified with acetic acid to give white crystals. After recrystallization from alcohol the compound melted at192°Cto 194°C. 

Chemical Name 7-Chloro-1 -dihydro-5-phenyl-l (2H)-1,4-benzodiazepin-2-one Common Name Nordiazepam desmethyidiazepam Structural Formula ... 

Chloro-1 -dihvdro-5-phenvl-2H-1,4-benzodiazepin-2-one-4-oxide Acetic anhydride Sodium hydroxide... 

A) Suspend lOg of 7-chloro-l -dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide in 150 ml of acetic anhydride and warm on a steam bath with stirring until all the solid has dissolved. Cool and filter off crystalline, analytically pure 3-acetoxy-7-chloro-1,3-dihydro-5-phenyl-2H-1 /t-benzodiazepin-2-one, melting point 242°C to 243°C. 

Chemical Name 7-Ch oro-5-phenyl-5 -methyltetrahydrooxazolo[54-b] -2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-one... 

Acetoxy-7[Pg.1610]

Azido-l, 4-benzodiazepin-2-ones 43 arc obtained from 1,4-benzodiazepin-2-ones by treatment with potassium bis(trimethylsilyl)amide, followed by 2,4,6-triisopropylbenzencsulfonyl azide. The azides are reduced to the corresponding amino compounds 44 by the action of triphenyl-phosphane in aqueous tetrahydrofuran. No further details were reported.429... 

RN 439-14-5 MF Cj HijClN O MW 284,75 EINECS 207-122-5 CN 7-chloro-1,3-dihydro-1 -methyl-5-phenyl-2//-1,4-benzodiazepin-2-one... 

Benzodiazepin-2-ones are converted efficiently into the 3-amino derivatives by reaction with triisopropylbenzenesulfonyl (trisyl) azide followed by reduction <96TL6685>. Imines from these amines undergo thermal or lithium catalysed cycloaddition to dipolarophiles to yield 3-spiro-pyrrolidine derivatives <96T13455>. Thus, treatment of the imine 50 (R = naphthyl) with LiBr/DBU in the presence of methyl acrylate affords 51 in high yield. 

Fig. 2 Squares Solubility of 7-chloro-l,3-hydro-5-phenyl-2H-1, 4-benzodiazepine-2-one-4-oxide in aqueous propylene glycol. (Data from Ref. 9) Circles Solubility of another benzodiazepine. (Unpublished data.)...

The reaction product (543) of diethyl malonate and diethyl chlorophos-phate was reacted with 1,4-benzodiazepin-2-ones in the presence of sodium hydride in THF at ambient temperature to give (l,4-benzdiazepin-2-ylidene)malonates (544) (81EUP38423). 

Scheme 3.5 Synthesis of 1,4-benzodiazepin-2-ones (83) by cyclative cleavage [172].

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