53251-94-8

Basic information

• Product Name: Pinaverium bromide
• Synonyms: 4-[(2-Bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2-(6,6-dimethylbicyclo[3.1.1]-hept-2-yl)ethoxy]ethyl]morpholinium Bromide;Dicetel;LAT-1717;Pinaverium;4-[(2-Bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2-(7,7-dimethyl-2-bicyclo[3.1.1]heptanyl)ethoxy]ethyl]morpholin-4-ium bromide;Pinaverium bromide;4-[(2-Bromo-4,5-dimethoxyphenyl)methyl]-4-[2-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethoxy]ethyl]-, bromide;4-[(2-Bromo-4,5-dimethoxy-phenyl)methyl]-4-[2-[2-(6,6-dimethylnorpinan-2-yl)ethoxy]ethyl]-1-oxa-4-azoniacyclohexane bromide
• CAS NO: 53251-94-8
• Molecular Formula: Br*C₂₆H₄₁BrNO₄
• Molecular Weight: 591.42
• EINECS: 258-450-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 53251-94-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 159-1640C
• Appearance: white crystalline powder
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Pinaverium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Pinaverium bromide(53251-94-8)
• EPA Substance Registry System: Pinaverium bromide(53251-94-8)

Safety Data

• Hazardous Substances Data: 53251-94-8(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Powder

Uses

Different sources of media describe the Uses of 53251-94-8 differently. You can refer to the following data:
1. Spasmolytic agent with low incidence of anticholinergic effects. Antispasmodic
2. Spasmolytic agent with low incidence of anticholinergic effects. Antispasmodic.

InChI:InChI=1/C26H41BrNO4.BrH/c1-26(2)21-6-5-19(22(26)16-21)7-11-31-12-8-28(9-13-32-14-10-28)18-20-15-24(29-3)25(30-4)17-23(20)27;/h15,17,19,21-22H,5-14,16,18H2,1-4H3;1H/q+1;/p-1

Synthetic route

1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene (53207-00-4) + 4-{2-[2-(6,6-dimethyl-norpinan-2-yl)-ethoxy]-ethyl}-morpholine (38284-47-8) → Pinaverium bromide (53251-94-8)

Conditions	Yield
In butanone Solvent; Reflux;	92.1%

N-chloroacetylmorpholine (1440-61-5) → Pinaverium bromide (53251-94-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C 2: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 0 °C 3: butanone / Reflux View Scheme

nopol (128-50-7) → Pinaverium bromide (53251-94-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: palladium on activated charcoal; hydrogen / ethanol / 20 °C 2: sodium hydride / tetrahydrofuran / 0 - 20 °C 3: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 0 °C 4: butanone / Reflux View Scheme

dihydronopol (4747-61-9) → Pinaverium bromide (53251-94-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C 2: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 0 °C 3: butanone / Reflux View Scheme

Upstream product

• 4747-61-9 dihydronopol 
• 128-50-7 nopol 
• 1440-61-5 N-chloroacetylmorpholine 
• 53207-00-4 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene 
• 38284-47-8 4-{2-[2-(6,6-dimethyl-norpinan-2-yl)-ethoxy]-ethyl}-morpholine 

Relevant articles and documents

A synthesis method of pinaverium bromide

The invention relates to a pinaverium bromide synthesis method. Cheap and easily available morpholine as a raw material and an acylating agent undergo a reaction to produce a novel intermediate and pinaverium bromide is synthesized from the intermediate under mild conditions. Raw material reaction is complete, side reaction is less, the pinaverium bromide has treatment cis-isomeride content greater than or equal to 99% and trans-isomer content less than or equal to 1%, and product cis-isomer content is greatly improved.