13230-84-7

Usage

InChI:InChI=1/C11H14ClNO/c1-13(11(14)9-12)8-7-10-5-3-2-4-6-10/h2-6H,7-9H2,1H3

Upstream product

• 79-04-9 chloroacetyl chloride 
• 589-08-2 N-Methyl-N-phenethylamine 
• 103-63-9 1-phenyl-2-bromoethane 

Downstream Products

• 73644-95-8 1,2,4,5-tetrahydro-3-methyl-3H-3-benzazepin-2-one 
• 73645-03-1 1,2,4,5-tetrahydro-1-(2,3-dimethoxybenzyl)-3-methyl-3H-3-benzazepin-2-one 
• 73645-01-9 1,2,4,5-tetrahydro-1-benzyl-3-methyl-3H-3-benzazepin-2-one 
• 73645-05-3 1,2,4,5-tetrahydro-1-cyclohexyl-3-methyl-3H-3-benzazepin-2-one 
• 425386-58-9 (1S)-1-amino-3-methyl-1H,4H,5H-benzo[d]azaperhydroepin-2-one di-p-toluoyl-L-tartrate 
• 425663-71-4 (1S)-1-amino-3-methyl-1H,4H,5H-benzo[d]azaperhydroepin-2-one hydrochloride 
• 253324-92-4 (1R)-1-amino-3-methyl-1H,4H,5H-benzo[d]azaperhydroepin-2-one 
• 253324-92-4 (1S)-1-amino-3-methyl-1H,4H,5H-benzo[d]azaperhydroepin-2-one 
• 253324-91-3 1-amino-3-methyl-1H,4H,5H-benzo-[d]azaperhydroepin-2-one 

Relevant academic research and scientific papers

Classical and dynamic resolution of 1-amino-3-methyl-1,3,4,5- tetrahydrobenzo[d]azepin-2-one

Two efficient production processes of enantioenriched 1-amino-3-methyl-1,3, 4,5-tetrahydro-benzo[d]azepin-2-one 1 were achieved using the readily available starting materials. A key step in the methodologies is a classical resolution or a dynamic resolution that provides excellent chemical (>80%) yields and enantiomeric excesses (>99.8% ee). The classical resolution was developed on a preparative scale while the dynamic resolution was implemented on a pilot plant scale.

HETEROCYCLIC COMPOUNDS, MEDICAMENTS CONTAINING SAID COMPOUNDS, USE THEREOF AND PROCESSES FOR THE PREPARATION THEREOF

The present invention relates to compounds of general formula (I) and the tautomers and the salts thereof, particularly the pharmaceutically acceptable salts thereof, which have valuable pharmacological properties, particularly an inhibitory effect on epithelial sodium channels, the use thereof for the treatment of diseases, particularly diseases of the lungs and airways.

BENZOLACTAMS-1. ALKYLATION OF 1,2,4,5-TETRAHYDRO-3-METHYL-3H-3-BENZAZEPIN-2-ONE WITH SODIUM HYDRIDE AND ALKYL HALIDE

Alkylation of 1,2,4,5-tetrahydro-3-methyl-3H-3-benzazepin-2-one 1a with various halides and sodium hydride in tetrahydrofuran-dimethylformamide solvent system was studied.Primary halides predominantly provided the 1-mono-substituted products, such as alkyl (2a-g,p,q), allyl (2j,k), propargyl (2l) and benzyl (2m-o) derivatives, in satisfactory yields, and secondary halides resulted in lower yields (2h,i) than primary halides.In attempted dialkylations with ω,ω'-dibromoalkanes, 5- and 6-membered spiro products (4c,d) were obtained by this method.The Michael type addition reaction was also studied and it was found that acrylic acid esters gave the corresponding adducts (2p,q).