3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-one

3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-one Basic information
Product Name:3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-one
Synonyms:MOLINDONE;3-ethyl-1,5,6,7-tetrahydro-2-methyl-5-(4-morpholinylmethyl)-4h-indol-4-on;3-ethyl-1,5,6,7-tetrahydro-2-methyl-5-(4-morpholinylmethyl)-4h-indol-4-one;3-Ethyl-2-methyl-6-(4-morpholinylmethyl)-1,5,6,7-tetrahydro-4H-indol-4-one;3-ethyl-6,7-dihydro-2-methyl-5-(morpholinomethyl)-indol-4(5h)-on;3-Ethyl-6,7-dihydro-2-methyl-5-(morpholinomethyl)indol-4(5H)-one;EN-1733A;indol-4(5h)-one
CAS:7416-34-4
MF:C16H24N2O2
MW:276.37
EINECS:
Product Categories:
Mol File:7416-34-4.mol
3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-one Structure
3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-one Chemical Properties
Melting point 180-181°
Boiling point 462.9±45.0 °C(Predicted)
density 1.140±0.06 g/cm3(Predicted)
solubility H2O: 19 mg/mL
form solid
pkapKa 6.9(H2O,t =25,I=0.2) (Uncertain)
color off-white
CAS DataBase Reference7416-34-4(CAS DataBase Reference)
NIST Chemistry ReferenceIndol-4(5h)-one, 3-ethyl-6,7-dihydro-2-methyl-5-(morpholinomethyl)-(7416-34-4)
Safety Information
Hazard Codes Xn
Risk Statements 22
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS NM3325000
Hazardous Substances Data7416-34-4(Hazardous Substances Data)
3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-one Usage And Synthesis
OriginatorMoban,Endo,US,1974
UsesMolindone is a more active antipsychotic than chloropromzine. Its sedative effect is less expressed. Side effects are also expressed less than with powerful neuroleptics. It facilitates the reduction of spontaneous movements and aggressiveness, and is used for treatment of psychotic disturbances, particularly in cases of chronic and severe schizophrenia.
UsesAntipsychotic.
DefinitionChEBI: Molindone is a member of indoles.
Manufacturing ProcessDiethyl ketone may be reacted with methyl nitrite and that product in turn reacted with cyclohexan-1,3-dione to give 3-ethyl-4,5,6,7-tetrahydro-2- methyl-4-oxoindole.
3-ethyl-4,5,6,7-tetrahydro-2-methyl-4-oxoindole 14.1 g (0.08 mol), 14.8 g morpholine hydrochloride (0.12 mol), and 3.6 g paraformaldehyde (0.12 mol) were refluxed in 200 ml ethanol for 40 hours. The solution was evaporated to dryness in vacuo on a steam bath and the residue digested with a mixture of 150 ml water and 10 ml 2N HCl. An insoluble residue of unreacted starting material was filtered off. To the acid solution, ammonia water was added dropwise with stirring and the amine crystallized out. It was purified by dissolving in 1N HCl and addition of ammonia, then by 2 crystallizations from benzene followed by 2 crystallizations from isopropanol, to yield 3-ethyl- 4,5,6,7-tetrahydro-2-methyl-4-oxoindole, melting point 180°C to 181°C.
Brand nameMoban (Endo).
Therapeutic FunctionAntipsychotic
Side effectsMolindone hydrochloride, a tetrahydro-indolone derivative, is a neuroleptic agent that is structurally unrelated to any of the other marketed neuroleptics. Molindone is less potent than haloperidol at blocking D2 receptors; however, it nonetheless can produce extrapyramidal side effects.
SynthesisMolindone, 3-ethyl-6,7-dihydro-2-methyl-5-(morpholinomethyl)indol-4(5H)- one (6.4.3), is synthesized by the nitrozation of diethylketone using nitric acid or methylnitrite into nitrozodiethylketone (6.4.1). Reduction of this product with zinc in acetic acid into 2-aminodiethylketone in the presence of cyclohexandion-1,3 gives 3-ethyl-2-methyl- 4,5,6,7-tetrahydroindol-4-one (6.4.2). Aminomethylation of this product using morpholine and formaldehyde gives molindone (6.4.3) [51¨C52].

Synthesis_7416-34-4

MetabolismMetabolism studies in humans show molindone to be rapidly absorbed and metabolized when given orally. There are 36 recognized metabolites, with less than 2 to 3% unmetabolized molindone being excreted in urine and feces. Clinical studies show that the antipsychotic effects of molindone last more than 24 hours, suggesting that one or more metabolites may contribute to its activity in vivo (62).
3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-one Preparation Products And Raw materials
Raw materials3-Pentanone-->Paraformaldehyde-->Nitrous acid methyl ester-->Bis(4-hydroxyphenyl) Sulfone-->MORPHOLINIUM CHLORIDE
6-CHLORO-1-INDANONE 96 N-Bromosuccinimide 1,3-Indanedione 5-Fluoro-1-indanone MOLINDONE HYDROCHLORIDE 3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-one 3-ethyl-2-methyl-4,5,6,7-tetrahydroindol-4-one MOLINDONE HCL INULIN 1,5,6,7-TETRAHYDRO-4H-INDOL-4-ONE N-ISOBUTYLMORPHOLINE MOLINDONE HYDROCHLORIDE (500 MG)

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