1-Cinnamoylpiperazine

Base Information

• Chemical Name: 1-Cinnamoylpiperazine
• CAS No.: 84935-37-5
• Molecular Formula: C₁₃H₁₆N₂O
• Molecular Weight: 216.283
• European Community (EC) Number: 671-432-0
• NSC Number: 133368
• Nikkaji Number: J1.894.801J
• Wikidata: Q76310509
• Mol file: 84935-37-5.mol

Synonyms:1-cinnamoylpiperazine;55486-27-6;1-Cinnamoyl-piperazine;3-phenyl-1-(piperazin-1-yl)prop-2-en-1-one;84935-37-5;(E)-3-phenyl-1-piperazin-1-ylprop-2-en-1-one;MFCD02093523;(E)-3-Phenyl-1-(piperazin-1-yl)prop-2-en-1-one;1-[(2e)-3-phenylprop-2-enoyl]piperazine;1-(3-Phenylacryloyl)piperazine;cinnamoyl piperazine;NSC133368;1-(cinnamoyl)piperazine;(2e)-3-phenyl-1-(piperazin-1-yl)prop-2-en-1-one;SCHEMBL2909559;AKOS000126377;FS-1227;NSC-133368;CS-0319355;MLS-0472351.0001;A830669

Chemical Property of 1-Cinnamoylpiperazine

Chemical Property:

• Vapor Pressure: 2.8E-07mmHg at 25°C
• Boiling Point: 420.5°C at 760 mmHg
• Flash Point: 208.1°C
• PSA: 32.34000
• Density: 1.116g/cm³
• LogP: 1.39830
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 216.126263138
• Heavy Atom Count: 16
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

1-(CINNAMOYL)PIPERAZINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)C(=O)C=CC2=CC=CC=C2
• Isomeric SMILES: C1CN(CCN1)C(=O)/C=C/C2=CC=CC=C2

Technology Process of 1-Cinnamoylpiperazine

There total 4 articles about 1-Cinnamoylpiperazine 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:

tert-butyl 4-(3-phenylpropanoyl)piperazine-1-carboxylate → (E)-3-phenyl-1-(piperazin-1-yl)prop-2-en-1-one (84935-37-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 12 h / 0 - 23 °C / Inert atmosphere

2.1: n-butyllithium; N-cyclohexyl-2,6-diisopropylaniline / tetrahydrofuran; hexane / 0.5 h / -40 °C / Cooling with ice; Inert atmosphere

2.2: 0.5 h / Cooling with ice; Inert atmosphere

2.3: 3 h / Cooling with ice; Heating; Inert atmosphere

With n-butyllithium; N-cyclohexyl-2,6-diisopropylaniline; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jacs.5b12924

Reference yield:

hydrocinnamic acid chloride (645-45-4) → (E)-3-phenyl-1-(piperazin-1-yl)prop-2-en-1-one (84935-37-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 14 h / 0 - 23 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 12 h / 0 - 23 °C / Inert atmosphere

3.1: n-butyllithium; N-cyclohexyl-2,6-diisopropylaniline / tetrahydrofuran; hexane / 0.5 h / -40 °C / Cooling with ice; Inert atmosphere

3.2: 0.5 h / Cooling with ice; Inert atmosphere

3.3: 3 h / Cooling with ice; Heating; Inert atmosphere

With n-butyllithium; N-cyclohexyl-2,6-diisopropylaniline; triethylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jacs.5b12924

Reference yield:

benzaldehyde (100-52-7) → 3-phenyl-1-(piperazin-1-yl)prop-2-en-1-one (55486-27-6,84935-37-5)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; piperidine / 2 h / 100 °C

2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 24 h / Reflux

3: triethylamine / dichloromethane / 0 °C

With piperidine; pyridine; thionyl chloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bioorg.2021.105139

upstream raw materials:

benzaldehyde

hydrocinnamic acid chloride

Downstream raw materials:

C₂₁H₁₉N₇O

C₂₂H₂₀N₆O

Refernces

• 1、 Chen, Yifeng,Turlik, Aneta,Newhouse, Timothy R.. "Amide α,β-Dehydrogenation Using Allyl-Palladium Catalysis and a Hindered Monodentate Anilide". . p. 1166 - 1169. Retrieved 2016/02/18.