(R)-2-((R)-6,7-Dimethoxy-1-(4-(trifluoromethyl)phenethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-N-methyl-2-phenylacetamide

Base Information

• Chemical Name: (R)-2-((R)-6,7-Dimethoxy-1-(4-(trifluoromethyl)phenethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-N-methyl-2-phenylacetamide
• CAS No.: 913358-93-7
• Molecular Formula: C29H31F3N2O3
• Molecular Weight: 549.033
• Mol file: 913358-93-7.mol

Synonyms:AlMorexant (hydrochloride);(alphaR,1S)-3,4-Dihydro-6,7-dimethoxy-N-methyl-alpha-phenyl-1-[2-[4-(trifluoromethyl)phenyl]ethyl]-2(1H)-isoquinolineacetamide monohydrochloride;Almorexant HCI;(R)-2-((S)-1-(4-(trifluoromethyl)phenethyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-N-methyl-2-phenylacetamide hydrochloride

Chemical Property of (R)-2-((R)-6,7-Dimethoxy-1-(4-(trifluoromethyl)phenethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-N-methyl-2-phenylacetamide

Chemical Property:

• PSA: 50.80000
• LogP: 6.87270
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

AlmorexantHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Almorexant Hydrochloride is an orally active orexin antagonist (OX1 and OX2 dual receptor antagonist) used in the treatment of insomnia.

Technology Process of (R)-2-((R)-6,7-Dimethoxy-1-(4-(trifluoromethyl)phenethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-N-methyl-2-phenylacetamide

There total 3 articles about (R)-2-((R)-6,7-Dimethoxy-1-(4-(trifluoromethyl)phenethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-N-methyl-2-phenylacetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(1S)-6,7-dimethoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline hydrochloride (1296659-30-7) + (S)-2-(methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonate (871224-68-9) → almorexant hydrochloride (913358-93-7)

Guidance literature:

(1S)-6,7-dimethoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline hydrochloride; With sodium carbonate; In butanone; at 20 ℃; for 0.166667h;

(S)-2-(methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonate; In butanone; for 16h; Reflux;

With hydrogenchloride; In ethyl acetate; at 60 ℃; for 1h; Product distribution / selectivity; Reflux;

Reference yield:

almorexant (871224-64-5) → almorexant hydrochloride (913358-93-7)

Guidance literature:

With hydrogenchloride; In methylisobutylketone (MIBK); water;

Reference yield:

(S)-2-(methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonate (871224-68-9) + (S)-6,7-dimethoxy-1-(4-(trifluoromethyl)phenethyl)-1,2,3,4-tetrahydroisoquinoline acetate (1169801-28-8) → almorexant hydrochloride (913358-93-7)

Guidance literature:

(S)-6,7-dimethoxy-1-(4-(trifluoromethyl)phenethyl)-1,2,3,4-tetrahydroisoquinoline acetate; With sodium hydroxide; In 4-methyl-2-pentanone; at 20 ℃;

(S)-2-(methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonate; With potassium carbonate; sodium hydroxide; In water; 4-methyl-2-pentanone; at 70 - 90 ℃;

With hydrogenchloride; In water; 4-methyl-2-pentanone;

upstream raw materials:

almorexant

(S)-2-(methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonate

(S)-6,7-dimethoxy-1-(4-(trifluoromethyl)phenethyl)-1,2,3,4-tetrahydroisoquinoline acetate

(1S)-6,7-dimethoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Refernces

• 1、 -. "CRYSTALLINE AND AMORPHOUS FORMS OF ALMOREXANT AND A METHOD OF THEIR PREPARATION". Page/Page column 5-6. . Retrieved 2011/06/23.
• 2、 -. "PROCESS FOR THE PREPARATION OF AN ENANTIOMERIC TRISUBSTITUTED 3,4-DIHYDRO-ISOQUINOLINE DERIVATIVE". Page/Page column 7; 14. . Retrieved 2010/12/29.