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59729-31-6

59729-31-6 Structure

59729-31-6 Structure
IdentificationBack Directory
[Name]

Lorcainide
[CAS]

59729-31-6
[Synonyms]

R-15889
Lopantrol
Lorcamide
Lorcainide
Ro-13。1042
Lorivox:Remivox
Lorcainide USP/EP/BP
N-(4-chlorophenyl)-2-phenyl-N-(1-propan-2-ylpiperidin-4-yl)acetamide
N-(4-Chlorophenyl)-N-[1-(1-methylethyl)-4-piperidinyl]benzeneacetamide
N-(4-Chlorophenyl)-N-[1-(1-methylethyl)piperidin-4-yl]benzeneacetamide
BenzeneacetaMide,N-(4-chlorophenyl)-N-[1-(1-Methylethyl)-4-piperidinyl]-
[Molecular Formula]

C22H27ClN2O
[MDL Number]

MFCD00242744
[MOL File]

59729-31-6.mol
[Molecular Weight]

370.921
Chemical PropertiesBack Directory
[Melting point ]

263 °C
[Boiling point ]

503.0±50.0 °C(Predicted)
[density ]

1.161±0.06 g/cm3(Predicted)
[pka]

9.48±0.20(Predicted)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

p-Toluenesulfonic acid-->Methyl acrylate-->Potassium borohydride-->Isopropylamine-->6-Benzylaminopurine-->4-Chloroaniline-->Phenylacetyl chloride-->1-Isopropyl-4-piperidone-->1-Aminopiperidine-->Solid Sodium methoxide-->Hydrochloric acid-->2-Bromopropane
Hazard InformationBack Directory
[Originator]

Remivox,Janssen,W. Germany,1980
[Uses]

Cardiac depressant (anti-arrhythmic).
[Definition]

ChEBI: Lorcainide is a member of acetamides.
[Manufacturing Process]

To a stirred suspension of 5 parts of N-(4-chlorophenyl)-N-(4-piperidinyl) benzeneacetamide, 5 parts of sodium carbonate, a few crystals of potassium iodide in 200 parts of butanol is added dropwise 4 parts of 2-bromopropane at room temperature. After the addition is complete, the whole is stirred and refluxed for 20 hours. Then the second portion of 4 parts of 2-bromopropane is added and stirring and refluxing is continued for another 19 hours. The reaction mixture is cooled, filtered and the filtrate is evaporated. From the oily free base, the hydrochloride salt is prepared in the conventional manner in 1,1'-oxybisethane and 2-propanone. The precipitated solid salt is filtered off and crystallized from a mixture of 2-propanone and 2-propanol, yielding 2 parts of N-(4-chlorophenyl)-N-[1-(1-methylethyl)-4-piperidinyl] benzeneacetamide hydrochloride; melting point 263°C.
[Therapeutic Function]

Antiarrhythmic
[Side effects]

Side effects include insomnia and gastrointestinal disturbances.
Safety DataBack Directory
[Toxicity]

LD50 in male mice, male and female rats (mg/kg): 18.8, 19.3, 18.6 i.v.; 483, 395, 435 orally (Barton, Marsboom)
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