56839-43-1

Basic information

• Product Name: Eperisone hydrochloride
• Synonyms: EPERISONE HCL;EPERISONE HYDROCHLORIDE;(4'-ethyl-2-methyl-3-piperidino)propiophenone hydrochloride;1-(4-ethylphenyl)-2-methyl-3-(1-piperidinyl)-1-propanonhydrochloride;4’-ethyl-2-methyl-3-piperidino-propiophenonhydrochloride;e0646;e-646;empp
• CAS NO: 56839-43-1
• Molecular Formula: C₁₇H₂₅NO*ClH
• Molecular Weight: 295.85
• EINECS: 1308068-626-2
• Product Categories: Miscellaneous Biochemicals;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 56839-43-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 169-171°C
• Boiling Point: 386.8 °C at 760 mmHg
• Flash Point: 137.4 °C
• Appearance: White solid
• Density: 0.994g/cm³
• Vapor Pressure: 3.46E-06mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: Eperisone hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Eperisone hydrochloride(56839-43-1)
• EPA Substance Registry System: Eperisone hydrochloride(56839-43-1)

Safety Data

• Hazardous Substances Data: 56839-43-1(Hazardous Substances Data)

Usage

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

Uses

Different sources of media describe the Uses of 56839-43-1 differently. You can refer to the following data:
1. A spasmolytic agent related structurally to Tolperisone (T535475). Muscle relaxant (skeletal).
2. Used as antispasmodic

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

InChI:InChI=1/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

Synthetic route

1,3-DIOXOLANE (646-06-0) + 1-(4-ethylphenyl)-1-propanone (27465-51-6) + piperidine hydrochloride (6091-44-7) → eperisone hydrochloride (56839-43-1)

Conditions	Yield
With hydrogenchloride at 90℃; for 6.5h;	95%

formaldehyd (50-00-0) + 1-(2-ethylphenyl)propan-1-one (16819-79-7) + piperidine hydrochloride (6091-44-7) → eperisone hydrochloride (56839-43-1)

Conditions	Yield
In isopropyl alcohol at 90 - 100℃; for 5h;	67%

1-bromo-2-ethylbenzene (1973-22-4) → eperisone hydrochloride (56839-43-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 2 h / -5 - 5 °C 1.2: 20 °C 2.1: trifluoroacetic anhydride / dimethyl sulfoxide; dichloromethane / 3 h / -30 °C 3.1: isopropyl alcohol / 5 h / 90 - 100 °C View Scheme

eperisone hydrochloride (56839-43-1) → eperisone (64840-90-0)

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate Product distribution / selectivity;	79%

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1) + eperisone hydrochloride (56839-43-1) → indomethacin eperisone salt (1043449-09-7)

Conditions	Yield
With sodium hydroxide In methanol

diclofenac sodium (15307-79-6) + eperisone hydrochloride (56839-43-1) → diclofenac eperisone salt (1043449-45-1)

Conditions	Yield
In methanol Heating;

eperisone hydrochloride (56839-43-1) → (+)-1-(4-ethylphenyl)-2-methyl-3-piperidin-1-ylpropan-1-one hydrochloride + (-)-1-(4-ethylphenyl)-2-methyl-3-piperidin-1-ylpropan-1-one hydrochloride

Conditions	Yield
Stage #1: eperisone hydrochloride With isopropylamine In methanol; carbon dioxide; isopropyl alcohol Resolution of racemate; Stage #2: With hydrogenchloride In acetonitrile for 0.0833333h; Cooling with ice;

Upstream product

• 646-06-0 1,3-DIOXOLANE 
• 27465-51-6 1-(4-ethylphenyl)-1-propanone 
• 6091-44-7 piperidine hydrochloride 
• 1973-22-4 1-bromo-2-ethylbenzene 
• 50-00-0 formaldehyd 
• 16819-79-7 1-(2-ethylphenyl)propan-1-one 

Downstream Products

• 64840-90-0 eperisone 
• 1043449-45-1 diclofenac eperisone salt 
• 1043449-09-7 indomethacin eperisone salt 

Relevant articles and documents

Preparation method of Eperisone hydrochloride impurity F

The invention provides a preparation method of Eperisone hydrochloride impurity F, which comprises the following steps: 2-bromoethylbenzene is used as a raw material, 1- (2-ethylphenyl) propanol is obtained through Grignard reaction, 2-ethyl propiophenone is obtained through oxidation reaction, and finally the Eperisone hydrochloride impurity F is obtained through Mannich reaction of the 2-ethyl propiophenone, paraformaldehyde and piperidine hydrochloride by a one-pot method. The structure of the Eperisone hydrochloride impurity F is shown as a formula (I), the purity of theEperisone hydrochloride impurity F obtained by adopting the technical scheme provided by the invention can reach 99%, and the Eperisone hydrochloride impurity F can be used as a reference substance for experimental research.