[2-(4-chlorophenyl)quinolin-4-yl]-(2-piperidyl)methanol

Base Information

• Chemical Name: [2-(4-chlorophenyl)quinolin-4-yl]-(2-piperidyl)methanol
• CAS No.: 5428-80-8
• Molecular Formula: C21H21 Cl N2 O
• Molecular Weight: 352.864
• Hs Code.: 2933990090
• Mol file: 5428-80-8.mol

Synonyms:NSC13316

Chemical Property of [2-(4-chlorophenyl)quinolin-4-yl]-(2-piperidyl)methanol

Chemical Property:

• Vapor Pressure: 5.44E-13mmHg at 25°C
• Melting Point: 198-199.5 °C
• Boiling Point: 551.4°C at 760 mmHg
• PKA: 13.22±0.20(Predicted)
• Flash Point: 287.3°C
• PSA: 45.15000
• Density: 1.244g/cm³
• LogP: 5.05950

Purity/Quality:

99%, ^*data from raw suppliers

Vacquinol-1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Vacquinols are a new class of quinine-derivatives that stimulate death in glioblastoma cells by massive macropinocytotic vacuolization, ATP depletion, and cytoplasmic membrane rupture. A key effector of vacquinols is MAPK kinase 4 (MKK4). Vacquinol-1 is an activator of MKK4-dependent macropinocytotic cell death in glioblastoma cells. It induces ATP depletion in glioblastoma cells (IC50 = 3.14 μM at 1 day) without affecting fibroblasts, embryonic stem cells, or osteosarcoma cells. Vacquinol-1 is orally bioavailable with good brain penetrance and excellent pharmacokinetics. Oral administration of vacquinol-1 (20 mg/kg once daily for five days) substantially impairs the growth of engrafted glioblastoma cell tumors in mice and prolongs survival.
• Uses: Vacquinol-1 is in the vacquinol class of quinine derivatives that stimulate death in glioblastoma cells through massive macropinocytotic vacuolization, ATP depletion and eventual cytoplasmic membrane rupture.

Technology Process of [2-(4-chlorophenyl)quinolin-4-yl]-(2-piperidyl)methanol

There total 10 articles about [2-(4-chlorophenyl)quinolin-4-yl]-(2-piperidyl)methanol 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: 66.3%

(2-(4-Chlorophenyl)quinolin-4-yl) (piperidin-2-yl)methanone → [2-(4-chlorophenyl)quinolin-4-yl]-piperidin-2-yl-methanol (5428-80-8)

Guidance literature:

With sodium borohydrid; In ethanol; hexane; ethyl acetate;

Reference yield:

methyl‐2‐(4‐chlorophenyl)quinoline‐4‐carboxylate (80221-37-0) → [2-(4-chlorophenyl)quinolin-4-yl]-piperidin-2-yl-methanol (5428-80-8)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N,N,N,-tetramethylethylenediamine; ammonium chloride / tetrahydrofuran; cyclohexane

2: hydrogenchloride / 1,4-dioxane; dichloromethane

3: sodium borohydrid / ethanol; ethyl acetate; hexane

With hydrogenchloride; sodium borohydrid; N,N,N,N,-tetramethylethylenediamine; ammonium chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; cyclohexane; ethyl acetate;

Reference yield:

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → [2-(4-chlorophenyl)quinolin-4-yl]-piperidin-2-yl-methanol (5428-80-8)

Guidance literature:

Multi-step reaction with 5 steps

1: ethanol

3: N,N,N,N,-tetramethylethylenediamine; ammonium chloride / tetrahydrofuran; cyclohexane

4: hydrogenchloride / 1,4-dioxane; dichloromethane

5: sodium borohydrid / ethanol; ethyl acetate; hexane

With hydrogenchloride; sodium borohydrid; N,N,N,N,-tetramethylethylenediamine; ammonium chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; cyclohexane; ethyl acetate;

upstream raw materials:

ethyl 2-(4-chlorophenyl)quinoline-4-carboxylate

6-benzoylamino-hexanoic acid ethyl ester

2-(4-chloro-phenyl)-quinoline-4-carbonyl chloride

methyl‐2‐(4‐chlorophenyl)quinoline‐4‐carboxylate

Refernces