133163-28-7

Basic information

• Product Name: midodrine hydrochloride
• Synonyms: Acetamide, 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]-, monohydrochloride, (R)- (9CI)
• CAS NO: 133163-28-7
• Molecular Formula: C12H18N2O4
• Molecular Weight: 0
• EINECS: 255-945-3
• Mol File: 133163-28-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 529.9°Cat760mmHg
• Flash Point: 274.3°C
• Appearance: /
• Density: 1.204g/cm³
• Vapor Pressure: 4.64E-12mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: midodrine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: midodrine hydrochloride(133163-28-7)
• EPA Substance Registry System: midodrine hydrochloride(133163-28-7)

Safety Data

• Hazardous Substances Data: 133163-28-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16)

Upstream product

• 4530-20-5 BOC-glycine 
• 3600-87-1 desglymidodrine 
• 133163-28-7 midodrine hydrochloride 
• 177018-41-6 {[(R)-2-(2,5-Dimethoxy-phenyl)-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylcarbamoyl]-methyl}-carbamic acid benzyl ester 
• 176851-44-8 N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((phenylmethoxy)carbonylamino)essigsaeureamid 
• 176851-43-7 N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid 
• 177018-40-5 {[(R)-2-(2,5-Dimethoxy-phenyl)-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester 
• 133163-24-3 <2R-(2α(R*),3aα,4α,7α,7aα)>-N-<2-(2,5-Dimethoxyphenyl)-2-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-ethyl>-2-<<(1,1-dimethylethoxy)-carbonyl>-amino>-acetamid 
• 133092-73-6 <2R-(2α(S*),3aα,4α,7α,7aα)>-N-<2-(2,5-Dimethoxyphenyl)-2-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-ethyl>-2-<<(1,1-dimethylethoxy)-carbonyl>-amino>-acetamid 
• 176851-46-0 {[(S)-2-(2,5-Dimethoxy-phenyl)-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylcarbamoyl]-methyl}-carbamic acid benzyl ester 
• 177018-39-2 {[(S)-2-(2,5-Dimethoxy-phenyl)-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester 
• 60681-97-2 2-azido-N-(β-hydroxy-2',5'-dimethoxyphenethyl)acetamide 
• 42794-76-3 midodrine 

Relevant articles and documents

Aminoalcohols, III: Preparation of Enantiomerically Pure Pharmacologically Active N-Substituted β-Aminoalcohols

A synthesis of N-substituted β-aminoalcohols is described starting from enantiomerically pure O-MBF- or O-MBE-protected β-aminoalcohols which can be prepared via LiAlH4 reduction of O-protected cyanohydrines. - Keywords: 1,2-Amino-alcohols, enantiomerically pure; N-Alkylation; Clorprenaline; Propranolol; Midodrine

PROCESS FOR THE PREPARATION OF MIDODRINE, PHARMACEUTICALLY-ACCEPTABLE SALTS THEREOF AND INTERMEDIATES

The present invention provides for a novel process for the preparation of Midodrine or a pharmaceutically acceptable salt thereof comprising: (a) a step of reacting 2-amino-1-(2’,5’-dimethoxyphenyl) ethanol of formula (I) with an N-protected glycine of formula (II) containing an amino protecting group in the presence of 1,1’-carbonyldiimidazole (CDI); and (b) removing the amino protecting group by deprotection formula (I), formula (II), wherein R1 is a benzyl, triphenylmethyl, tert-butyloxycarbonyl, or a benzyloxycarbonyl group. This results in an unexpectedly efficient and cost-effective process. Additionally, the process is simple and safe as all the intermediates and reagents involved in the process pose no safety risks. Further reaction of Midodrine with a pharmaceutically acceptable acid affords a pharmaceutically acceptable salt thereof. Preferably, the pharmaceutically acceptable salt obtained from the process according to the present invention is Midodrine Hydrochloride.

Process for the synthesis of (+) 2-amino-n-{2, (2,5-dimethoxy phenyl)-2-hydroxyethyl} acetamide monohydrochloride

This invention relates to an improved process for synthesizing (±)-2-Amino-N-[2-(2,5-dimethoxyphenyl]-2-hydroxyethyl acetamide monohydrochloride in good yield and in a cost effective manner from 1-(2,5-dimethoxyphenyl)-2-bromoethanone by reacting the same