4579-60-6

Basic information

• Product Name: INETERMEDIATE OF GALANTHAMINE 1
• Synonyms: INETERMEDIATE OF GALANTHAMINE 1;N-(4-hydroxyphenethyl)-N-(3-hydroxy-4-methoxy)benzylamine;N-(p-Hydroxyphenethyl)-N-(3-hydroxy-4-methoxy)benzylamine;5-(((2-(4-HYDROXYPHENYL)ETHYL)AMINO)METHYL)-2-METHOXYPHENOL;Nsc77594;INETERMEDIATE OF GALANTHAMINE
• CAS NO: 4579-60-6
• Molecular Formula: C₁₆H₁₉NO₃
• Molecular Weight: 273.327
• Product Categories: Chemical Amines;Amines;Aromatics
• Mol File: 4579-60-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 183-1850C
• Boiling Point: 471.8°Cat760mmHg
• Flash Point: 239.1°C
• Appearance: /
• Density: 1.192g/cm³
• Vapor Pressure: 1.79E-17mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: INETERMEDIATE OF GALANTHAMINE 1(CAS DataBase Reference)
• NIST Chemistry Reference: INETERMEDIATE OF GALANTHAMINE 1(4579-60-6)
• EPA Substance Registry System: INETERMEDIATE OF GALANTHAMINE 1(4579-60-6)

Safety Data

• Hazardous Substances Data: 4579-60-6(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

N-(p-Hydroxyphenethyl)-N-(3-hydroxy-4-methoxy)benzylamine (cas# 4579-60-6) is a compound useful in organic synthesis.

InChI:InChI=1/C27H26N2O4/c30-23-16-22-21(15-26(32)33-25(22)17-24(23)31)18-28-11-13-29(14-12-28)27(19-7-3-1-4-8-19)20-9-5-2-6-10-20/h1-10,15-17,27,30-31H,11-14,18H2

Upstream product

• 51-67-2 tyrosamine 
• 621-59-0 isovanillin 
• 50773-56-3 3-benzyloxy-4-hydroxybenzaldehyde 
• 6272-38-4 O-benzylcatechol 
• 102686-18-0 5-{[(E)-2-(4-Hydroxy-phenyl)-ethylimino]-methyl}-2-methoxy-phenol 

Downstream Products

• 26668-50-8 2,2,2-trifluoro-N-(3-hydroxy-4-methoxybenzyl)-N-(4-hydroxyphenethyl)acetamide 
• 26722-77-0 noroxomaritidine 
• 510-77-0 (-)-narwedine 
• 122584-19-4 N-(p-hydroxyphenylethyl)-N-(3-hydroxy-4-methoxybenzyl)amine hydrochloride 
• 122584-18-3 N-(4-hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide 
• 122584-17-2 N-(3-hydroxy-4-methoxybenzyl)-N-(4-hydroxyphenethyl)formamide 

Relevant articles and documents

Synthesis, biological evaluation and molecular modeling studies of substitutedN-benzyl-2-phenylethanamines as cholinesterase inhibitors

In this work, we report the synthesis of a series of derivatives ofN-benzyl-2-phenylethanamine which is the framework of norbelladine, the natural common precursor of the Amaryllidaceae alkaloids. These compounds were assessed in the inhibition of both AChE and BChE which are the enzymes responsible for the breakdown of acetylcholine and hence they constitute targets in the palliative treatment of Alzheimer's disease. In particular, brominated derivatives exhibited the lowest IC50values against AChE. Interestingly, the presence of iodine in one of the aromatic rings highly increased the inhibition of BChE compared to its analogues, with an IC50value similar to that of galantamine, which is the reference compound currently used in the treatment of AD. A possible mechanism of action for these compounds was determined by molecular modeling studies using combined techniques of docking and molecular dynamics simulations.

Processes for the preparation of derivatives of 4a, 5, 9, 10, 11, 12-hexahydro-6H-benzofuro-[3a, 3, 2-ef][2]benzazepine

The invention relates to processes for the preparation of 4a,5,9,10,11,12-hexahydro-6H-benzofuro[3a,3,2-ef][2]benzazepine, or derivatives thereof. Furthermore, the invention also relates to the compounds formed during the preparation of 4a, 5,9,10,11,12-hexahydro-6H-benzofuro[3a,3,2-ef][2]benzazepine.

An improved synthesis of galanthamine

Modifications in the total synthesis of the Amarylidaceae alkaloid of galanthamine from commercially available isovanillin and tyramine have resulted in a shortened reaction sequence, which is amenable to upscaling and in improved product yield.