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56839-43-1

56839-43-1 Structure

56839-43-1 Structure
IdentificationMore
[Name]

Eperisone hydrochloride
[CAS]

56839-43-1
[Synonyms]

(4'-ethyl-2-methyl-3-piperidino)propiophenone hydrochloride
EPERISONE HCL
EPERISONE HYDROCHLORIDE
1-(4-ethylphenyl)-2-methyl-3-(1-piperidinyl)-1-propanonhydrochloride
4’-ethyl-2-methyl-3-piperidino-propiophenonhydrochloride
e0646
e-646
empp
mional
myonal
Eperison hcl
Eperison Hydrochloride
EPERISON HYDROCHLORIDE,JP14
Eperizone hydrochloride
1-Propanone, 1-(4-ethylphenyl)-2-methyl-3-(1-piperidinyl)-, hydrochloride
Akitonal
Atines
[EINECS(EC#)]

1308068-626-2
[Molecular Formula]

C17H26ClNO
[MDL Number]

MFCD00941459
[Molecular Weight]

295.85
[MOL File]

56839-43-1.mol
Questions And AnswerBack Directory
[Synthesis]

The product was synthesized by reacting p-ethylphenylacetone (2) with guanethidine hydrochloride via the Mannieh reaction, as shown in Figure 1:
Reaction route for the synthesis of ethylperisone hydrochloride
Figure 1 shows the reaction route for the synthesis of ethylperisone hydrochloride
Synthesis method:
1. Synthesis of p-ethylphenylacetone (2)
Propyl chloride (100g, 1.08 mol) was added. After treatment, the reaction solution was distilled under reduced pressure after recovering petroleum ether and excess ethylbenzene. The fraction at bP112-114 ℃/1.33kPa was collected to obtain 2.

2. Synthesis of ethylparaben (1)
Take freshly distilled ethylparaben (20.2 g, 0.24 mol), add anhydrous ethanol (20 ml), add concentrated hydrochloric acid dropwise at low temperature to pH 4-5, evaporate the ethanol under reduced pressure, then add anhydrous ethanol (50 ml), p-ethyl acetone (32.4 g, 0.2 mol), 36% formaldehyde solution (42.0 g, 0.5 mol) and concentrated hydrochloric acid (1 ml), stir and reflux for 8 h, evaporate the solvent, dissolve the residue in 10% sodium hydroxide solution, extract with ether, wash the extract with water, dry, and pass hydrogen chloride through in an ice-water bath to pH 2-3. Filter out the generated solid, recrystallize with ethanol-acetone to obtain 1 colorless crystal.
Chemical PropertiesBack Directory
[Melting point ]

169-171°C
[storage temp. ]

Inert atmosphere,Room Temperature
[solubility ]

Methanol (Slightly), Water (Slightly)
[form ]

Solid
[color ]

White
[InChI]

InChI=1S/C17H25NO.ClH/c1-3-15-7-9-16(10-8-15)17(19)14(2)13-18-11-5-4-6-12-18;/h7-10,14H,3-6,11-13H2,1-2H3;1H
[InChIKey]

GTAXGNCCEYZRII-UHFFFAOYSA-N
[SMILES]

C1(=CC=C(CC)C=C1)C(=O)C(C)CN1CCCCC1.Cl
[CAS DataBase Reference]

56839-43-1(CAS DataBase Reference)
Hazard InformationBack Directory
[Description]

Eperisone hydrochloride is a centrally acting muscle relaxant useful in the management of various spastic conditions including cervical spondylosis and cerebral palsy. It is structurally related to tolperisone.
[Chemical Properties]

White Solid
[Originator]

Eisai (Japan)
[Uses]

A spasmolytic agent related structurally to Tolperisone (T535475). Muscle relaxant (skeletal).
[Uses]

Used as antispasmodic
[Definition]

ChEBI: Eperisone hydrochloride is an aromatic ketone.
[Manufacturing Process]

To 60 ml of isopropanol, there are introduced 120 g of 4-ethyl-propiophenone, 28.8g of p-formaldehyde and 107 g of piperidine hydrochloride, and the resulting mixture is heated to reflux on an oil bath with stirring. The heating is continued, and when the reaction mixture solidifies, the state being a sign of completion of the reaction, there are added 500 ml of acetone thereinto. The solidified mass is pulverized by crush, recovered by filtration and washed with acetone. 144 g of the crude dry crystalline substance is thus obtained, which is the hydrochloride of the purposed product. The hydrochloride is recrystallized from isopropanol, and there are obtained the crystalline needles having the melting point of 170°C to 172°C.
[Brand name]

MYONAL
[Therapeutic Function]

Muscle relaxant
Safety DataBack Directory
[Toxicity]

LD50 in male S.D. rats, Wistar rats, mice (mg/kg): 1300, 1850, 1024 orally (Miyagawa)
Spectrum DetailBack Directory
[Spectrum Detail]

Eperisone hydrochloride(56839-43-1)1HNMR
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