6027-23-2

Basic information

• Product Name: Hordenine hydrochloride
• Synonyms: anhalinehydrochloride;dimethyl-beta-(4-hydroxyphenyl)ethylaminehydrochloride;eremursinehydrochloride;hordeninehydrochloride;n,n-dimethyltyraminehydrochloride;p-(2-(dimethylamino)ethyl)-phenohydrochloride;p-(2-dimethylaminoethyl)phenolhydrochloride;peyocactinehydrochloride
• CAS NO: 6027-23-2
• Molecular Formula: C₁₀H₁₅NO*ClH
• Molecular Weight: 201.69
• EINECS: 227-892-6
• Product Categories: Herb extract
• Mol File: 6027-23-2.mol

Chemical Properties

• Melting Point: 178 °C
• Boiling Point: 270.2 °C at 760 mmHg
• Flash Point: 123.5 °C
• Appearance: /
• Vapor Pressure: 0.00417mmHg at 25°C
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Hordenine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Hordenine hydrochloride(6027-23-2)
• EPA Substance Registry System: Hordenine hydrochloride(6027-23-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 6027-23-2(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C10H15NO.ClH/c1-11(2)8-7-9-3-5-10(12)6-4-9;/h3-6,12H,7-8H2,1-2H3;1H

Synthetic route

N,N-dimethyl-p-hydroxyphenylacetamide → 2-(4-methoxyphenyl)-N,N-dimethylethylamine hydrochloride (6027-23-2)

Conditions	Yield
Stage #1: N,N-dimethyl-p-hydroxyphenylacetamide With sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex In tetrahydrofuran at 50 - 60℃; for 4h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Concentration; Reagent/catalyst;	81.2%

1-[2-(dimethylamino)ethyl]-4'-methoxy-2,3-dihydro-[1,1′-biphenyl]-4(1H)-one (34603-52-6) → 2-(4-methoxyphenyl)-N,N-dimethylethylamine hydrochloride (6027-23-2)

Conditions	Yield
sublimation in the presence of NH4Cl;

2-(4-methoxyphenyl)-N,N-dimethylethylamine hydrochloride (6027-23-2) → N,N-dimethyltyramine (539-15-1)

Conditions	Yield
With hydrogen bromide at 120 - 130℃;	71.54%

4-bromo-2-fluorophenol (2105-94-4) + 2-chloro-5-((2-trimethylsilylethoxy)methoxy)pyridine (1235035-65-0) + (Z)-tert-butyl 3-(3-hydroxypropyl)-6-(8-(3-((2-(trimethylsilyl)ethoxy)methyl)benzo[d]thiazol-2(3H)-ylidenecarbamoyl)-3,4-dihydroisoquinolin-2(lH)-yl)picolinate (1235036-21-1) + 2-(4-methoxyphenyl)-N,N-dimethylethylamine hydrochloride (6027-23-2) → 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4-(2-dimethylaminoethyl)phenoxy)propyl)picolinic acid (1235034-29-3)

Conditions

Yield

Stage #1: 4-bromo-2-fluorophenol; (Z)-tert-butyl 3-(3-hydroxypropyl)-6-(8-(3-((2-(trimethylsilyl)ethoxy)methyl)benzo[d]thiazol-2(3H)-ylidenecarbamoyl)-3,4-dihydroisoquinolin-2(lH)-yl)picolinate With di-tert-butyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran for 2h; Stage #2: 2-chloro-5-((2-trimethylsilylethoxy)methoxy)pyridine With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 100℃; Stage #3: 2-(4-methoxyphenyl)-N,N-dimethylethylamine hydrochloride

Upstream product

• 34603-52-6 1-[2-(dimethylamino)ethyl]-4'-methoxy-2,3-dihydro-[1,1′-biphenyl]-4(1H)-one 
• 76472-23-6 N,N-dimethyl-p-hydroxyphenylacetamide 
• 539-15-1 N,N-dimethyltyramine 
• 14140-15-9 4-(2-bromoethyl)phenol 

Downstream Products

• 539-15-1 N,N-dimethyltyramine 
• 1235034-29-3 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4-(2-dimethylaminoethyl)phenoxy)propyl)picolinic acid 

Relevant articles and documents

Preparation method of hordenine hydrochloride

The invention discloses a preparation method of hordenine hydrochloride. The preparation method comprises the following steps: taking 4-(2-bromoethyl)phenol as a raw material, adding ethanol to prepare a solution, dropwise adding excessive dimethylamine solution, and stirring at a lower temperature to carry out amination reaction to obtain hordenine hydrobromide. The proper excessive dimethylamine is adopted, so that the quaternization side reaction is effectively inhibited, the solvent dispersion effect is also played, the contact reaction opportunity of the hordenine product generated in the first reaction and the 4-(2-bromoethyl)phenol added later is greatly reduced, the high product yield can be kept, and meanwhile the low preparation cost is achieved; 4-(2-bromoethyl) phenol is added into ethanol to prepare a dilute solution of ethanol, and the dilute solution of ethanol is dropwise added into a dimethylamine solution to improve the dispersity of 4-(2-bromoethyl) phenol in a reaction system and inhibit quaternization side reaction; and the amination reaction is carried out by stirring at a relatively low temperature of 10-25 DEG C, so that the occurrence of quaternization side reaction is inhibited, and a relatively good reaction effect is achieved.

Synthetic method of hordenine hydrochloride

The invention discloses a synthetic method of hordenine hydrochloride. According to the synthetic method of hordenine hydrochloride, methyl 4-hydroxyphenylacetate and dimethylamine are taken as raw materials, a protonic solvent and a polar aprotic solvent are taken as solvents so as to obtain N,N-dimethyl-4-hydroxybenzeneacetamide; N,N-dimethyl-4-hydroxybenzeneacetamide is taken as a raw material, tetrahydrofuran is taken as a solvent, and a reducing agent and a catalyst are added so as to obtain hordenine; hydrochloric acid is added, ethanol is taken as a solvent, and hordenine hydrochloride is obtained via reaction. In the synthetic method, methyl 4-hydroxyphenylacetate is taken as a raw material, hordenine hydrochloride is obtained via two-step synthesis, the raw materials are easily available, the synthesis method is simple, amplification production is convenient to realize, production cost is low, industrialized production is convenient to realize, and market potential is high.

THE BIOSYNTHESIS OF SCELETIUM ALKALOIDS IN SCELETIUM SUBVELUTINUM

Six Sceletium (Mesembrine) alkaloids (1)-(6) are identified, together with N,N-dimethyltyramine (10) as constituents of Sceletium subvelutinum.The alkaloids (1)-(6) incorporate label from radioactive tyramine (8) and 4-hydroxyphenylpropionic acid (12) as expected; notably -4-hydroxydihydrocinnamaldehyde is a more efficient alkaloid precursor than the acid (12).Preliminary evidence locates the amine (16) potentially as a key precursor for Sceletium alkaloids; (14) is less efficiently incorporated.