849-55-8

Basic information

• Product Name: NYLIDRIN HYDROCHLORIDE
• Synonyms: 1-p-hydroxyphenyl-2-(1’-methyl-3’-phenylpropylamino)-1-propanolhydrochloride;arlidinhydrochloride;bupheninehydrochloride;dilatolhydrochloride;dilatyl;p-hydroxy-alpha-(1-((1-methyl-3-phenylpropyl)amino)ethyl)-benzylalcohohyd;p-hydroxy-alpha-(1-((1-methyl-3-phenylpropyl)amino)ethyl)benzylalcoholhydro;suprifenpsbhydrochloride
• CAS NO: 849-55-8
• Molecular Formula: C₁₉H₂₅NO₂*ClH
• Molecular Weight: 335.87
• EINECS: 212-701-0
• Mol File: 849-55-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 198-199℃ (decomposition)
• Appearance: /
• CAS DataBase Reference: NYLIDRIN HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: NYLIDRIN HYDROCHLORIDE(849-55-8)
• EPA Substance Registry System: NYLIDRIN HYDROCHLORIDE(849-55-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: DO8300000
• Hazardous Substances Data: 849-55-8(Hazardous Substances Data)

Usage

Chemical Properties

White, crystals or powder, odorless; tasteless. Slightly soluble in water and alcohol; very slightly soluble in chloroform, ether; pH of 1% solution is between 4.5 and 6.5.

Originator

Buphenine hydrochloride,Troponwerke

Uses

Medicine (treatment of heart disease).

Manufacturing Process

The p-benzoxy-α-bromopropiophenone and 1-phenyl-3-amino-butane were heating for an hour on the water bath in the absence of solvents. A solid crystalline cake was obtained. After being extracted with boiling acetic acid, the hydrobromide of 1-(p-hydroxyphenyl)-2-(β-phenylbutylamino)propanone-1 was obtained. The hydrobromide of 1-(p-hydroxyphenyl)-2-(β-phenylbutylamino)propanone- 1 was suspended in very pure methanol and shaken with a 10% palladium hydroxide barium sulfate catalyst in contact with, hydrogen. After rather more than 2 mols of hydrogen had been taken-up the hydrogenation stopped. The 1-(p-hydroxyphenyl)-2-(3-phenylbutylamino)propanol-1, was filtered, washed with methanol and evaporated, melting point 110-111°C.

InChI:InChI=1/C19H25NO2.ClH/c1-14(8-9-16-6-4-3-5-7-16)20-15(2)19(22)17-10-12-18(21)13-11-17;/h3-7,10-15,19-22H,8-9H2,1-2H3;1H

Synthetic route

C26H29NO2*ClH → nylidrin hydrochloride (849-55-8)

Conditions	Yield
With 3% Pd/C; hydrogen In methanol at 20℃;	95%

1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone (35081-45-9) + (RS)-1-methyl-3-phenylpropylamine (22374-89-6) → nylidrin hydrochloride (849-55-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / ethyl acetate / 5 h / Reflux 2: 3% Pd/C; hydrogen / methanol / 20 °C View Scheme

Upstream product

• 35081-45-9 1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone 
• 22374-89-6 (RS)-1-methyl-3-phenylpropylamine 
• 96072-82-1 C₂₆H₂₉NO₂*ClH 

Relevant articles and documents

Preparation method for buphienine hydrochloride

The invention relates to a preparation method for buphienine hydrochloride. The preparation method comprises the step of preparing an intermediate IV and the buphienine hydrochloride. The method provided by the invention is simple and convenient to operate and applicable to industrial production; the purity of a product is high; and the quality of the product reaches the use standards of human pharmaceutic preparations.