51072-35-6

Basic information

• Product Name: 3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl]isoquinoline
• Synonyms: 3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl]isoquinoline
• CAS NO: 51072-35-6
• Molecular Formula: C₁₇H₂₁NO
• Molecular Weight: 255.35474
• EINECS: 256-949-8
• Mol File: 51072-35-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 404.4°C at 760 mmHg
• Flash Point: 160.2°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 2.21E-06mmHg at 25°C
• Refractive Index: 1.585
• PKA: 8.14±0.20(Predicted)
• CAS DataBase Reference: 3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl]isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl]isoquinoline(51072-35-6)
• EPA Substance Registry System: 3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl]isoquinoline(51072-35-6)

Safety Data

• Hazardous Substances Data: 51072-35-6(Hazardous Substances Data)

Usage

Uses

1-(p-Methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinoline is a useful synthetic compound.

InChI:InChI=1/C17H21NO/c1-19-15-8-6-13(7-9-15)12-17-16-5-3-2-4-14(16)10-11-18-17/h6-9H,2-5,10-12H2,1H3

Upstream product

• 30356-08-2 (S)-1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxyphenyl)methyl]isoquinoline 
• 3399-73-3 2-(1-cyclohexenyl)ethylamine 
• 104-01-8 4-Methoxyphenylacetic acid 
• 51072-34-5 N-(2-cyclohex-1-enylethyl)-2-(4-methoxyphenyl)-acetamide 

Downstream Products

• 51072-36-7 (+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 74570-02-8 (+)-1-(p-hydroxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 74570-02-8 4-((S)-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 152-02-3 levallorphan 
• 71-82-9 levallorphan tartarate 
• 30356-08-2 (S)-1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxyphenyl)methyl]isoquinoline 
• 30356-07-1 (1S)-1-[(4-methoxyphenyl)methyl]-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 67596-84-3 (+)-2-methyl-1-(4-methoxy)benzyl-1,2,3,4,5,6,7,8-hexahydroisoquinoline 
• 125-71-3 dextromethorphan 
• 28973-48-0 (+)-3-methoxy-N-formylmorphinan 
• 51773-23-0 (R)-2-Formyl-1-<(4-methoxyphenyl)methyl>-1,2,3,4,5,6,7,8-octahydroispquinoline 
• 29144-31-8 (S)-2-Formyl-1-<(4-methoxyphenyl)methyl>-1,2,3,4,5,6,7,8-octahydroispquinoline 
• 116172-20-4 (Z)-2-Formyl-1-<(4-methoxyphenyl)methylene>-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 116172-19-1 (E)-2-Formyl-1-<(4-methoxyphenyl)methylene>-1,2,3,4,5,6,7,8-octahydroisoquinoline 

Relevant articles and documents

Racemization recovery method of dextromethorphan hydrobromide intermediate byproducts

A racemization recovery method of dextromethorphan hydrobromide intermediate byproducts comprises the following steps: 1) performing mother liquor treatment: under a stirring condition, carrying out reduced pressure distillation until methanol is basically evaporated completely, when the temperature of the concentrated mother liquor is lower than 40 DEG C, adding a sodium hydroxide solution, stirring, standing, detecting that the pH value is greater than 12, layering, recovering mandelic acid by using the obtained water phase, concentrating the obtained oil phase under reduced pressure until toluene is completely evaporated, and cooling to 65-80 DEG C; 2) performing N-chlorination: adding isopropanol, and dropwise adding a sodium hypochlorite solution; 3) performing racemization: adding liquid caustic soda into the reaction system, and stirring for reaction; 4) reducing: dropwise adding a sodium borohydride solution, and reacting completely; 5) performing chiral resolution: adding methanol and D-mandelic acid into the toluene solution of a compound (I), and carrying out chiral resolution; and (6) refining the mother liquor: treating the mother liquor obtained in step (5) as a raw material according to the treatment methods in steps (1)-(4) to obtain a mother liquor prepared compound (I) methylbenzene solution, and adding oxalic acid for refining.

A process for preparing dextromethorphan method

The invention relates to a novel method for preparing dextromethorphan. When the method is used for preparing an intermediate (+)-1-(4-methoxy) benzyl-1,2,3,4,5,6,7,8-hexahydroisoquinoline (VI), a catalytic reducing method is adopted to carry out chiral reduction on 1-(4-methoxy) benzyl-3,4,5,6,7,8-hexahydroisoquinoline (VI), so that the intermediate is prepared with high selectivity. The novel method disclosed by the invention can cancel complex operations such as chiral resolution, is simple to operate, gentle in reaction condition, short in total time, wide in material source, and very suitable for industrially producing dextromethorphan.

Racemization recycling method for byproduct in resolution mother liquor of dextromethorphan hydrobromide midbody

The invention relates to a racemization recycling method for a resolution byproduct in a dextromethorphan hydrobromide midbody 1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxy phenyl) methyl] isoquinoline. The racemization recycling method is characterized by comprising the following steps: (1) resolving racemic 1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxy phenyl) methyl] isoquinoline by using D-mandelic acid or D-tartaric acid so as to obtain D-mandelic acid or D-tartrate and 1,2,3,4,5,6,7,8-octahydro-R-1-[(4-methoxy phenyl) methyl] isoquinoline of a 1,2,3,4,5,6,7,8-octahydro-S-1-[(4-methoxy phenyl) methyl] isoquinoline compound; (2) oxidizing the 1,2,3,4,5,6,7,8-octahydro-R-1-[(4-methoxy phenyl) methyl] isoquinoline so as to obtain 1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxy phenyl) methyl] isoquinoline; (3) reducing the 1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxy phenyl) methyl] isoquinoline, thereby obtaining the dextromethorphan midbody 1,2,3,4,5,6,7,8-octahydro-1-[(4-methoxy phenyl) methyl] isoquinoline. The racemization recycling method for the byproduct, namely, a levogyration midbody of dextromethorphan, is gentle in condition, simple and convenient to operate and small in material consumption.