(alphaE)-alpha-[(3,4-Dihydroxy-5-nitrophenyl)methylene]-beta-oxo-1-piperidinepropanenitrile

Base Information

• Chemical Name: (alphaE)-alpha-[(3,4-Dihydroxy-5-nitrophenyl)methylene]-beta-oxo-1-piperidinepropanenitrile
• CAS No.: 1150310-15-8
• Molecular Formula: C₁₅H₁₅N₃O₅
• Molecular Weight: 317.301
• Mol file: 1150310-15-8.mol

Synonyms:(2E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(piperidin-yl-1-carbonyl)prop-2-ennitrile

Chemical Property of (alphaE)-alpha-[(3,4-Dihydroxy-5-nitrophenyl)methylene]-beta-oxo-1-piperidinepropanenitrile

Chemical Property:

• Melting Point: 207-208℃ (ethanol )

Purity/Quality:

99% ^*data from raw suppliers

(αE)-α-[(3,4-Dihydroxy-5-nitrophenyl)methylene]-β-oxo-1-piperidinepropanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (αE)-α-[(3,4-Dihydroxy-5-nitrophenyl)methylene]-β-oxo-1-piperidinepropanenitrile is an impurity of Entacapone (E558500), a peripherally acting inhibitor of catechol-O-methyl transferase (COMT), an enzyme involved in the metabolism of catecholamine neurotransmitters and related drugs. Antiparkinsonian.

Technology Process of (alphaE)-alpha-[(3,4-Dihydroxy-5-nitrophenyl)methylene]-beta-oxo-1-piperidinepropanenitrile

There total 5 articles about (alphaE)-alpha-[(3,4-Dihydroxy-5-nitrophenyl)methylene]-beta-oxo-1-piperidinepropanenitrile 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: 67.0%

1-cyanoacetylpiperidine (15029-30-8) + 3,4-dihydroxy-5-nitrobenzaldehyde (116313-85-0) → (2E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(piperidin-yl-1-carbonyl)prop-2-ennitrile (1150310-15-8)

Guidance literature:

With piperidine; acetic acid; In toluene; Reflux;

DOI:10.1016/j.bmcl.2009.02.081

Reference yield:

3,4-dihydroxy-5-nitrobenzaldehyde (116313-85-0) → (2E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(piperidin-yl-1-carbonyl)prop-2-ennitrile (1150310-15-8)

Guidance literature:

Multi-step reaction with 3 steps

1: piperidine; acetic acid / ethanol / 4 h / 80 °C

2: thionyl chloride / 25 - 80 °C

3: 0 °C

With piperidine; thionyl chloride; acetic acid; In ethanol; 1: Knoevenagel condensation;

DOI:10.1080/00397911.2010.539894

Reference yield:

piperidine (110-89-4) → (2E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(piperidin-yl-1-carbonyl)prop-2-ennitrile (1150310-15-8)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 0 - 20 °C

2: ammonium acetate / methanol / 3 h / Reflux

With ammonium acetate; In methanol; dichloromethane;

upstream raw materials:

1-cyanoacetylpiperidine

3,4-dihydroxy-5-nitrobenzaldehyde

piperidine

(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-2-propenoyl chloride

Refernces

• 1、 Srikanth,Ray, Uttam Kumar,Srinivas Rao,Gupta, P. Badarinadh,Lavanya,Islam, Aminul. "Efficient approach to pure entacapone and related compounds". experimental part. p. 1359 - 1366. Retrieved 2012/04/04.