122584-18-3

Usage

Uses

Used in Organic Synthesis:
N-(p-Hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide is used as a synthetic intermediate for the development of various organic compounds. Its chemical properties allow it to be a valuable building block in the creation of complex molecules, which can be further utilized in different applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(p-Hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide is used as a key component in the synthesis of new drugs. Its unique structure can be exploited to design and develop novel therapeutic agents with potential applications in treating various diseases.
Used in Chemical Research:
N-(p-Hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide is also used in chemical research as a model compound to study various reaction mechanisms and to understand the behavior of similar molecules. This knowledge can be applied to develop new synthetic methods and improve existing ones.
Used in Material Science:
In the field of material science, N-(p-Hydroxyphenethyl)-N-(2-bromo-5-hydroxy-4-methoxybenzyl)formamide can be used as a precursor to develop new materials with specific properties. Its unique chemical structure can be tailored to create materials with desired characteristics, such as improved stability, reactivity, or selectivity.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C17H18BrNO4/c1-23-17-9-15(18)13(8-16(17)22)10-19(11-20)7-6-12-2-4-14(21)5-3-12/h2-5,8-9,11,21-22H,6-7,10H2,1H3

Upstream product

• 122584-17-2 N-(3-hydroxy-4-methoxybenzyl)-N-(4-hydroxyphenethyl)formamide 
• 179107-93-8 N-(p-hydroxyphenylethyl)-N-(6-bromo-3-hydroxy-4-methoxybenzyl)amine 
• 109-94-4 formic acid ethyl ester 
• 2973-59-3 2-bromoisovanillin 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 621-59-0 isovanillin 
• 51-67-2 tyrosamine 
• 4579-60-6 N-(p-hydroxyphenylethyl)-N-(3-hydroxy-4-methoxybenzyl)amine 
• 102686-18-0 5-{[(E)-2-(4-Hydroxy-phenyl)-ethylimino]-methyl}-2-methoxy-phenol 

Downstream Products

• 510-77-0 (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one 
• 510-77-0 (-)-narwedine 
• 1953-04-4 Galantamine hydrobromide 
• 2973-59-3 2-bromoisovanillin 
• 13062-78-7 N-[2-(4-hydroxyphenyl)ethyl]formamide 
• 122584-14-9 N-formyl-1-bromo-narwedine 

Relevant academic research and scientific papers

Development of a pilot scale process for the anti-alzheimer drug (-)-galanthamine using large-scale phenolic oxidative coupling and crystallisation-induced chiral conversion

(-)-Galanthamine has been synthesised using an efficient nine-step procedure, which in large scale affords 12.4 (6.7-19.1)% overall yield. The process improvements and optimization of each step are described. Notable steps include (i) an oxidative phenol coupling and (ii) crystallisation-induced chiral conversion of (±)-narwedine to (-)-narwedine. This is a practical and cost-effective synthesis of (-)-galanthamine which is amenable to pilot plant scale-up to afford sufficient material for use in clinical trials.

Biomimetic synthesis of galantamine: Via laccase/TEMPO mediated oxidative coupling

Laccase-mediated intramolecular oxidative radical coupling of N-formyl-2-bromo-O-methylnorbelladine afforded a novel and isolable spirocyclohexadienonic intermediate of galantamine. High yield and conversion of substrate were obtained in the presence of the redox mediator 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). This laccase procedure, with an overall yield of 34%, represents a scalable and environmentally friendly alternative to previously reported syntheses of galantamine based on the use of potassium ferricyanide as an unspecific radical coupling reagent.

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.

New kilogram-synthesis of the anti-Alzheimer drug (-)-galanthamine

A concise, scalable synthesis of (-)-galanthamine, a drug being used for the treatment of Alzheimer's disease, is described. The yield of the critical phenolic coupling step was optimized to 45-50%. For the reduction of the aryl bromide, air-activated LiAlH4 was used and racemic narwedine was converted to (-)-narwedine by a second order asymmetric transformation.

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.