Piperanine

Base Information

• Chemical Name: Piperanine
• CAS No.: 23512-46-1
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• European Community (EC) Number: 803-489-6
• NSC Number: 125180
• Nikkaji Number: J1.060.547D,J16.564F
• Wikidata: Q76303594
• Pharos Ligand ID: FAC6W5NV3XMX
• Metabolomics Workbench ID: 46256
• ChEMBL ID: CHEMBL256218
• Mol file: 23512-46-1.mol

Synonyms:Piperanine;Piperanin;23512-46-1;4,5-Dihydroxypiperine;(E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpent-2-en-1-one;Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2-pentenyl)-, (E)-;Piperidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2-pentenyl]-, (E)-;Da,b-Dihydropiperine;NSC125180;b-Hydropiperylpiperidine;Dalpha,Beta-Dihydropiperine;MLS002473216;CHEMBL256218;MEGxp0_000204;SCHEMBL15159492;SCHEMBL23728300;ACon1_000146;N17H21NO3;Delata-Alpha,Beta-Dihydropiperine;CHEBI:167837;QHWOFMXDKFORMO-XVNBXDOJSA-N;HMS2270O08;BDBM50415870;N17-H21-N-O3;NSC-125180;Piperanine, >=95% (LC/MS-ELSD);NCGC00180838-01;65937-41-9;SMR001397304;BRD-K72444591-001-01-1;1-[5-(3,4-Methylenedioxyphenyl)-2-pentenoyl]piperidine;1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2-pentenyl]piperidine;5-(3,4-Methylenedioxyphenyl)-2-pentenoic acid piperidide;trans-5-(3,4-methylenedioxyphenyl)-2-pentenoic acid piperidide;(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one;(E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one;2-Penten-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E)-;Piperidine, 1-[(2E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2-pentenyl]-;Piperidine, 1-[5-[3,4-(methylenedioxy)phenyl]-2-pentenoyl]-, (E)-

Chemical Property of Piperanine

Chemical Property:

• Melting Point: 78 °C
• Boiling Point: 489.9±45.0 °C(Predicted)
• PKA: -0.79±0.20(Predicted)
• Density: 1.178±0.06 g/cm3(Predicted)
• Storage Temp.: ?20°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 287.15214353
• Heavy Atom Count: 21
• Complexity: 376

Purity/Quality:

99% ^*data from raw suppliers

Piperanine ≥95% (LC/MS-ELSD) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(CC1)C(=O)C=CCCC2=CC3=C(C=C2)OCO3
• Isomeric SMILES: C1CCN(CC1)C(=O)/C=C/CCC2=CC3=C(C=C2)OCO3

Technology Process of Piperanine

There total 8 articles about Piperanine 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: 70.0%

piperidine (110-89-4) + 3-(3,4-methylenedioxyphenyl)propionaldehyde (30830-55-8) + Bestmann ylide (73818-55-0,15596-07-3) → piperanine (23512-46-1)

Guidance literature:

In tetrahydrofuran; for 24h; Heating;

DOI:10.1039/b105745f

Reference yield: 14.0%

piperidine (110-89-4) + 3-(3',4'-methylenedioxyphenyl)-2-penten-1-oic acid (222321-54-2) → piperanine (23512-46-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.3390/molecules14093833

Reference yield:

3-(benzo[d][1,3]dioxol-5-yl)propan-1-ol (7031-03-0) → piperanine (23512-46-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / PDC / CH₂Cl₂ / 20 °C

2: 70 percent / tetrahydrofuran / 24 h / Heating

With dipyridinium dichromate; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b105745f

upstream raw materials:

piperidine

3-(3',4'-methylenedioxyphenyl)-2-penten-1-oic acid

3-(3,4-methylenedioxyphenyl)propionaldehyde

Bestmann ylide

Downstream raw materials:

tetrahydropiperine

Refernces

• 1、 Pedersen, Mikael E.,Metzler, Bjorn,Stafford, Gary I.,Van Staden, Johannes,Jaeger, Anna K.,Rasmussen, Hasse B.. "Amides from Piper capense with CNS activity - A preliminary SAR analysis". experimental part. p. 3833 - 3843. Retrieved 2009/12/26.