(Z)-Cinnarizine

Base Information

• Chemical Name: (Z)-Cinnarizine
• CAS No.: 750512-44-8
• Molecular Formula: C26H28N2
• Molecular Weight: 368.522
• Mol file: 750512-44-8.mol

Synonyms:(Z)-Cinnarizine;(Z)-1-(DiphenylMethyl)- 4-(3-phenyl-2-propenyl)piperazine;1-(DiphenylMethyl)-4-[(2Z)-3-phenyl-2-propen-1-yl]piperazine;cis-Cinnarizine;Cinnarizine EP IMpurity B

Chemical Property of (Z)-Cinnarizine

Chemical Property:

• PSA: 6.48000
• LogP: 4.98280
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

(Z)-Cinnarizine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The Z-isomer of Cinnarizine (C465300). (Z)-Cinnarizine (Cinnarizine EP Impurity B) is a Z-isomer of Cinnarizine (C465300).

Technology Process of (Z)-Cinnarizine

There total 6 articles about (Z)-Cinnarizine 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: 72.8%

1-benzhydryl-4-(2-acetaldehyde)piperazine (1522375-86-5) + benzyltriphenylphosphonium chloride (1100-88-5) → (Z)-1-(diphenylmethyl)-4-cinnamylpiperazine (750512-44-8,16699-20-0) + cinnarizine (298-57-7,16699-20-0)

Guidance literature:

With potassium tert-butylate; In dichloromethane; at 5 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1080/00397911.2013.826808

Reference yield:

diphenylmethylpiperazine (841-77-0) → (Z)-1-(diphenylmethyl)-4-cinnamylpiperazine (750512-44-8,16699-20-0) + cinnarizine (298-57-7,16699-20-0)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; potassium iodide / 85 - 90 °C

2: hydrogen bromide; water / 20 °C

3: potassium tert-butylate / dichloromethane / 5 °C / Inert atmosphere

With potassium tert-butylate; water; hydrogen bromide; potassium carbonate; potassium iodide; In dichloromethane; 3: |Wittig Olefination;

DOI:10.1080/00397911.2013.826808

Reference yield:

benzophenone (119-61-9) → (Z)-1-(diphenylmethyl)-4-cinnamylpiperazine (750512-44-8,16699-20-0) + cinnarizine (298-57-7,16699-20-0)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium tetrahydroborate / methanol / 20 °C

2: tetrabutylammomium bromide; hydrogenchloride / water; toluene / 40 - 45 °C

3: toluene / 60 - 100 °C

4: potassium carbonate; potassium iodide / 85 - 90 °C

5: hydrogen bromide; water / 20 °C

6: potassium tert-butylate / dichloromethane / 5 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; potassium tert-butylate; tetrabutylammomium bromide; water; hydrogen bromide; potassium carbonate; potassium iodide; In methanol; dichloromethane; water; toluene; 6: |Wittig Olefination;

DOI:10.1080/00397911.2013.826808

upstream raw materials:

diphenylmethylpiperazine

benzophenone

1-(diphenylmethyl)-4-(2,2-dimethoxyethyl)piperazine

1-benzhydryl-4-(2-acetaldehyde)piperazine

Downstream raw materials:

(Z)-1-(diphenylmethyl)-4-cinnamylpiperazine dihydrochloride