99614-64-9

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,9-TETRAHYDRO-9-METHTYL-3-METHYLENE-4H-CARBAZOL-4-ONE is used as an impurity in Ondansetron (O655000) for the purpose of understanding and controlling the quality and safety of the medication. This is important to ensure that the drug is effective and free from harmful contaminants.

InChI:InChI=1/C14H13NO/c1-9-7-8-12-13(14(9)16)10-5-3-4-6-11(10)15(12)2/h3-6H,1,7-8H2,2H3

Upstream product

• 50-00-0 formaldehyd 
• 27387-31-1 9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 506-59-2 N,N-dimethylammonium chloride 
• 153139-56-1 3-[(dimethylamino)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one 
• 294863-10-8 ethyl 3-(1-methyl-1H-indol-2-yl)propanoate 
• 88221-09-4 ethyl 3-(1-methyl-1H-indol-2-yl)acrylate 
• 27421-51-8 1-methyl-1H-indole-2-carboxaldehyde 
• 603-76-9 1-methylindole 
• 99614-02-5 ondanserton 
• 110-91-8 morpholine 
• 880-09-1 di(N-piperidinyl)methane 
• 102-53-4 bis-(diethylamino)methane 
• 68922-17-8 1,1'-methylenebis(3-methylpiperidine) 
• 51-80-9 bis-(dimethylamino)methane 

Downstream Products

• 99614-02-5 ondanserton 

Relevant academic research and scientific papers

C(sp2)-H Bond Multiple Functionalization in Air for Construction of Tetrahydrocarbazoles with Continuous Quaternary Carbons and Polycyclic Diversification

The C(sp2)-H function of indole ketone with diazo compound via a rhodium(II)-catalyzed intramolecular electrophilic trapping reaction under mild conditions in air was demonstrated. The established methodology provided a highly efficient approach for direct synthesis of mutisubstituted tetrahydrocarbazoles with continuous quaternary carbons. The resulting products facilitate further modification to conveniently construct tetrahydrocarbazoles with additional fused heterocyclic rings. By phenotypic screening, several products exhibit good anticancer bioctivities in osteosarcoma cell lines.

Preparation method of ondansetron impurity A

The invention discloses a preparation method of an ondansetron impurity A. The method comprises the following steps of firstly weighing ondansetron raw materials and a proper amount of aluminum chloride; adding a hydrogen peroxide water solution for dissolution to prepare the ondansetron solution, wherein the mass percentage of hydrogen peroxide in the hydrogen peroxide water solution is 12 percent; transferring the solution to a reaction kettle with a polytetrafluoroethylene inner liner; after the sealing, putting the reaction kettle into a baking oven for reaction for 8h at 140 DEG C; afterthe reaction is completed, cooling the materials into a room temperature; performing extraction by ethyl acetate; collecting the ethyl acetate part; performing concentration drying to obtain a hydrothermal reaction extract; then, performing separation and purification on the hydrothermal reaction extracts by an HSCCC method to obtain an impurity A. The method provided by the invention has the advantages that firstly through hydrothermal reaction, the ondansetron is degraded to obtain impurities A and D; the water is used as a medium; economical and environment-friendly effects are achieved; then, through HSCCC one step, the impurities A and D can be respectively obtained through separation and purification; the purity is 98 percent or higher.

A ONE-POT PROCESS FOR THE PREPARATION OF ANTIEMETIC AGENT, 1,2,3,9-TETRAHYDRO-9-METHYL-3[(2-METHYL)-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-O

A one-pot industrial process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazole-1-yl)methyl]-4H-carbazol-4-one of Formula-(I) from 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one of Formula-(IV) involves reaction of Formula (IV) with HNR1R2 salt and paraformaldehyde, where R1,R2 are independently alkyl groups or together forms a cyclic alkyl group, in a solvent system of acetic acid and hydrocarbon solvent to form a crude mixture of intermediate compounds of Formula (III) and (VIII), which is converted to ondansetron (Formula (I)) without isolation by reaction with 2-methyimidazole in a suitable solvent system in the same pot.

Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one and ondansetron therefrom

The present invention provides a rapid, high-yielding process for preparing 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one from 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one without using a secondary amine as a catalyst, and without using glacial acetic acid as a solvent. The present invention further provides a rapid, high-yielding process for preparing ondansetron from 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one without using alumina as a catalyst.

PROCESS FOR PREPARING 1,2,3,9-TETRAHYDRO-9-METHYL-3-[(2-METHYL-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-ONE OR ITS SALT

The present invention provides an improved process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one or its salt, which is useful as an anti-vomiting agent, in a high yield under a mild condition, so as to be favorably applied to a large-scale mass production thereof.

PROCESS FOR MAKING ONDANSETRON AND INTERMEDIATES THEREOF

The invention relates to a process for producing a compound of formula (I), wherein a carbazolone of formula II, formaldehyde or a formaldehyde precursor, an amine of formula III or a salt thereof wherein R1 and R2 each independently represent a C1 to C4 alkyl group or together with the nitrogen atom they form a 5- or 6-membered ring, and an imidazole of formula V or a salt thereof are reacted at elevated temperature in anon-aqueous polar solvent and in the presence of a water binding agent to form the compound of formula (I).

Process for the preparation of 1,2,3,9-tetrahydro-9-methyl-3-{(2-methyl-1H-imidazol-1-yl)methyl}-4H-carbazol-4-one

Pure -1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one or a pharmaceutically acceptable salt thereof is prepared in a high yield by a simple process which reacts 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one with a 2-methylimidazole derivative in an organic solvent or in a mixture of an organic solvent and water in the presence of a halosilane compound.

Process for the preparation of 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)-methyl)-4H-carbazol-4-one

Pure 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one or a pharmaceutically acceptable salt thereof is prepared in a high yield by a simple process which reacts 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one with a 2-methylimidazole derivative in an organic solvent or in a mixture of an organic solvent and water in the presence of a halosilane compound.

An efficient process of ondansetron synthesis

An efficient and practical two-step synthesis of ondansetron (1) was accomplished from readily available N-methyltetrahydrocarbazolone (2) via direct Mannich a-methylenation and alumina catalyzed Michael addition resulting in a 70% overall yield.

1,2,3,9-tetrahydro-3-imidazol-1-ylmethyl-4H-carbazol-4-ones, composition containing them, and method of using them to treat neuronal 5HT function disturbances

The invention relates to compounds of formula (I). STR1 wherein R 1 represents a hydrogen atom or a C 1-10 alkyl, C 3-7 cycloalkyl, C 3-6 alkenyl, C 3-7 cycloalkyl-(C 1-4) alkyl, C 3-10 alkynyl, phenyl or phenyl-C 1-3 alkyl group, and one of the groups represented by R 2, R 3 and R 4 is a hydrogen atom or a C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl or phenyl-(C 1-3) alkyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C 1-6 alkyl group; and physiologically acceptable salts and solvates, e.g. hydrates thereof.The compounds are potent selective antagonists at ""neuronal"" 5-hydroxytryptamine receptors and are useful in the treatment of migraine and psychotic disorders such as schizophrenia.