N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl}cyclohexylamine

Base Information

• Chemical Name: N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl}cyclohexylamine
• CAS No.: 506427-91-4
• Molecular Formula: C₂₃H₃₅Cl₂N₃O₂
• Molecular Weight: 456.456
• Mol file: 506427-91-4.mol

Synonyms:

Chemical Property of N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl}cyclohexylamine

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

trans-N-tert-Butoxycarbonyl-4-[2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl]cyclohexanamine 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: tert-Butyl ((1R,4R)-4-(2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethyl)cyclohexyl)carbamate is an intermediate for the synthesis of Desmethyl Cariprazine Hydrochloride (D291365), a derivative of Cariprazine (C183490) which is an orally active D2/D3 dopamine receptor antagonist (1,2,3). Cariprazine is an antipsychotic drug candidate for the potential treatment of schizophrenia, bipolar mania and depression.

Technology Process of N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl}cyclohexylamine

There total 42 articles about N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl}cyclohexylamine 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: 91.0%

1-(2,3-dichlorophenyl)piperazine (41202-77-1) + trans-2-(1-(4-(N-tert-butoxycarbonyl)amino)cyclohexyl)acetaldehyde (215790-29-7) → trans N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]ethyl}-cyclohexylamine (506427-91-4)

Guidance literature:

With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b00581

Reference yield: 83.1%

trans 2-{1-[4-(N-tert-butoxycarbonyl)amino]cyclohexyl}ethyl methanesulfonate + 1-(2,3-dichlorophenyl)piperazine (41202-77-1) → trans N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl}cyclohexylamine (506427-91-4)

Guidance literature:

In acetonitrile; for 4h; Reflux;

Reference yield: 82.0%

1-(2,3-dichlorophenyl)-piperazine hydrochloride (119532-26-2,864512-47-0) + trans (2-(1-[4-(N-(tert-butoxycarbonyl))-amino]-cyclohexyl))ethyl 4-methylbenzenesulfonate (2093293-77-5) → trans N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]ethyl}-cyclohexylamine (506427-91-4)

Guidance literature:

With potassium carbonate; In acetonitrile; for 8h; Reflux;

upstream raw materials:

1-(2,3-dichlorophenyl)-piperazine hydrochloride

1,1-dimethylethyl[trans-4-(2-oxoethyl)cyclohexyl]carbamate

1-(2,3-dichlorophenyl)piperazine

tert-butyl (trans-4-(2-aminoethyl)cyclohexyl)carbamate

Refernces

• 1、 éles, János,Bana, Péter,Fül?p, Zsolt,Greiner, István. "C-N bond formation by consecutive continuous-flow reductions towards a medicinally relevant piperazine derivative". supporting information. . Retrieved 2021/05/28.
• 2、 -. "Preparation method of cariprazine". Paragraph 0086-0091. . Retrieved 2020/07/02.