Diethyl 2,2'-(1-benzylpiperidine-4,4-diyl)diacetate

Base Information

• Chemical Name: Diethyl 2,2'-(1-benzylpiperidine-4,4-diyl)diacetate
• CAS No.: 160133-32-4
• Molecular Formula: C20H29NO4
• Molecular Weight: 347.455
• NSC Number: 116042
• DSSTox Substance ID: DTXSID40297457
• Wikidata: Q82038561
• Mol file: 160133-32-4.mol

Synonyms:160133-32-4;diethyl 2,2'-(1-benzylpiperidine-4,4-diyl)diacetate;NSC116042;SCHEMBL2206046;DTXSID40297457;PUUPUDJVNOJWNP-UHFFFAOYSA-N;NSC-116042;diethyl 1-benzylpiperidine-4,4-diacetate;CS-0447516;4,4-Piperidinediaceticacid,1-(phenylmethyl)-,4,4-diethylester;4,4-Piperidinediacetic acid, 1-(phenylmethyl)-, 4,4-diethyl ester

Chemical Property of Diethyl 2,2'-(1-benzylpiperidine-4,4-diyl)diacetate

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 347.20965841
• Heavy Atom Count: 25
• Complexity: 401

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC1(CCN(CC1)CC2=CC=CC=C2)CC(=O)OCC

Technology Process of Diethyl 2,2'-(1-benzylpiperidine-4,4-diyl)diacetate

There total 4 articles about Diethyl 2,2'-(1-benzylpiperidine-4,4-diyl)diacetate 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:

ethanol (64-17-5) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-[1-benzyl-4-(2-ethoxy-2-oxoethyl)-4-piperidyl]acetate (160133-32-4)

Guidance literature:

1-phenylmethyl-4-piperidone; ethyl 2-cyanoacetate; With ammonia; In methanol; at 0 ℃; for 120h;

With sulfuric acid; water; at 100 ℃; for 48h; Heating / reflux;

ethanol; With sulfuric acid; for 24h; Heating / reflux;

Reference yield:

9-benzyl-2,4-dioxo-3,9-diazaspiro[5,5]undecane-1,5-dicarbonitrile (189333-46-8) → ethyl 2-[1-benzyl-4-(2-ethoxy-2-oxoethyl)-4-piperidyl]acetate (160133-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. H₂SO₄ / 8.5 h / Heating

2: H₂SO₄ / 14 h / Heating

With sulfuric acid;

DOI:10.1021/jm030944+

Reference yield:

1-phenylmethyl-4-piperidone (3612-20-2) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-[1-benzyl-4-(2-ethoxy-2-oxoethyl)-4-piperidyl]acetate (160133-32-4)

Guidance literature:

In ethanol; sulfuric acid; ammonia; water; sodium carbonate;

upstream raw materials:

1-phenylmethyl-4-piperidone

9-benzyl-2,4-dioxo-3,9-diazaspiro[5,5]undecane-1,5-dicarbonitrile

ethanol

ethyl 2-cyanoacetate

Downstream raw materials:

1-benzylpiperidine-4,4-diethanol

1-(9-(3,3-difluoroazetidin-1-yl)-9-phenyl-3-azaspiro[5.5]undecan-3-yl)-2-(((S)-1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)ethanone

1-[3-(3-fluorophenyl)-3-pyrrolidin-1-yl-9-azaspiro[5.5]undecan-9-yl]-2-[1-[[3-(trifluoromethyl)phenyl]sulfonyl]-piperidin-2-yl]-ethanone

1-(9-(azetidin-1-yl)-9-phenyl-3-azaspiro[5.5]undecan-3-yl)-2-(((S)-1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)ethanone

Refernces

• 1、 Leonardi, Amedeo,Barlocco, Daniela,Montesano, Federica,Cignarella, Giorgio,Motta, Gianni,Testa, Rodolfo,Poggesi, Elena,Seeber, Michele,De Benedetti, Pier G.,Fanelli, Francesca. "Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α1d Adrenergic Receptor". . p. 1900 - 1918. Retrieved 2007/10/03.
• 2、 -. "Preparation of benzodiazepinone derivatives for treatment of cardiac arrhythmias and pharmaceutical composition containing them.". . . Retrieved 2008/06/13.