(3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl]cyclohexylmethyl}hexahydro-1H-4,7-methanisoindol-1,3-dione dihydrochloride

Base Information

• Chemical Name: (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl]cyclohexylmethyl}hexahydro-1H-4,7-methanisoindol-1,3-dione dihydrochloride
• CAS No.: 139563-25-0
• Molecular Formula: C₂₈H₃₆N₄O₂S*2ClH
• Molecular Weight: 565.607
• Mol file: 139563-25-0.mol

Synonyms:

Chemical Property of (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl]cyclohexylmethyl}hexahydro-1H-4,7-methanisoindol-1,3-dione dihydrochloride

Chemical Property:

Purity/Quality:

>95% ^*data from raw suppliers

exo-cis-LurasidoneHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: exo-cis-Lurasidone Hydrochloride is an impurity of the drug Lurasidone (L474920), an antipsychotic used for treatment of schizophrenia.

Technology Process of (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl]cyclohexylmethyl}hexahydro-1H-4,7-methanisoindol-1,3-dione dihydrochloride

There total 39 articles about (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl]cyclohexylmethyl}hexahydro-1H-4,7-methanisoindol-1,3-dione dihydrochloride 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: 98.3%

(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate (186204-37-5) + (3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione (14805-29-9,1318027-24-5) → (3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride (367514-88-3,139563-25-0)

Guidance literature:

(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate; (3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione; With potassium carbonate; In toluene; at 105 ℃; for 15h; Industrial scale;

With hydrogenchloride; In isopropyl alcohol; Industrial scale;

Reference yield: 96.1%

lurasidone (194861-74-0,367514-87-2,1318074-25-7) → (3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride (367514-88-3,139563-25-0)

Guidance literature:

With hydrogenchloride; In water; at 50 ℃; for 2h; Temperature;

Reference yield: 93.0%

hydrogenchloride (7647-01-0,15364-23-5) + lurasidone (194861-74-0,367514-87-2,1318074-25-7) → (3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride (367514-88-3,139563-25-0)

Guidance literature:

In water; isopropyl alcohol; at 65 - 75 ℃;

upstream raw materials:

lurasidone

(3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione

(3aR,7aR)-2,2-bis(2-hydroxyethyl)octahydro-1H-isoindolium mesylate

3-aminobenzisothiazole

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF LURASIDONE BASE AND ITS SALT". Paragraph 15. . Retrieved 2017/09/27.
• 2、 -. "Lurasidone key intermediate preparation method". . . Retrieved 2017/09/01.