(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(piperidin-1-yl)methanone

Base Information

• Chemical Name: (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(piperidin-1-yl)methanone
• CAS No.: 215923-54-9
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.294
• Hs Code.: 2934999090
• UNII: PV6YEC8983
• DSSTox Substance ID: DTXSID70175951
• Nikkaji Number: J1.630.116G
• Wikipedia: CX-546
• Wikidata: Q5014874
• ChEMBL ID: CHEMBL1255648
• Mol file: 215923-54-9.mol

Synonyms:1-(1,4-benzodioxan-6-ylcarbonyl)piperidine;CX-546;CX546

Chemical Property of (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(piperidin-1-yl)methanone

Chemical Property:

• Vapor Pressure: 2.34E-07mmHg at 25°C
• Refractive Index: 1.573
• Boiling Point: 422.8 °C at 760 mmHg
• PKA: -1.08±0.20(Predicted)
• Flash Point: 209.5 °C
• PSA: 38.77000
• Density: 1.215 g/cm³
• LogP: 2.02180
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 247.12084340
• Heavy Atom Count: 18
• Complexity: 301

Purity/Quality:

99% ^*data from raw suppliers

CX 546 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCN(CC1)C(=O)C2=CC3=C(C=C2)OCCO3
• Uses: CX546 has been used as positive allosteric modulator for the glutamatergic receptor α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) in mice.

Technology Process of (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(piperidin-1-yl)methanone

There total 5 articles about (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(piperidin-1-yl)methanone 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: 99.0%

piperidine (110-89-4) + 6-iodo-1,4-benzodioxane (57744-67-9) + chloroform (67-66-3,8013-54-5) → CX-546 (215923-54-9,205510-63-0)

Guidance literature:

With cesiumhydroxide monohydrate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; In toluene; at 80 ℃; for 24h; Glovebox; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.5b01385

Reference yield: 95.0%

piperidine (110-89-4) + carbon monoxide (201230-82-2) + 6-bromo-1,4-benzodioxane (52287-51-1) → CX-546 (215923-54-9,205510-63-0)

Guidance literature:

With potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In toluene; at 105 ℃; for 12h; under 3000.3 Torr;

DOI:10.1021/cs400232b

Reference yield: 83.0%

→ CX-546 (215923-54-9,205510-63-0)

Guidance literature:

upstream raw materials:

piperidine

carbon monoxide

6-bromo-1,4-benzodioxane

6-iodo-1,4-benzodioxane

Refernces

• 1、 Chiba, Shunsuke,Dixon, Darren J.,Fan, Dongyang,Ong, Derek Yiren. "Transition-Metal-Free Reductive Functionalization of Tertiary Carboxamides and Lactams for α-Branched Amine Synthesis". supporting information. p. 11903 - 11907. Retrieved 2020/05/22.
• 2、 Dang, Tuan T.,Zhu, Yinghuai,Ngiam, Joyce S. Y.,Ghosh, Subhash C.,Chen, Anqi,Seayad, Abdul M.. "Palladium nanoparticles supported on ZIF-8 as an efficient heterogeneous catalyst for aminocarbonylation". . p. 1406 - 1410. Retrieved 2013/07/26.