1-Ethylpiperazine-2,3-dione

Base Information

• Chemical Name: 1-Ethylpiperazine-2,3-dione
• CAS No.: 59702-31-7
• Molecular Formula: C6H10N2O2
• Molecular Weight: 142.158
• Hs Code.: 29339900
• European Community (EC) Number: 261-866-5
• UNII: GG5LCG550O
• DSSTox Substance ID: DTXSID80208421
• Nikkaji Number: J27.889K
• Wikidata: Q72474639
• Mol file: 59702-31-7.mol

Synonyms:1-ethyl-2,3-dioxopiperazine

Chemical Property of 1-Ethylpiperazine-2,3-dione

Chemical Property:

• Appearance/Colour: white to pale yellow crystalline powder
• Melting Point: 106-110 °C(lit.)
• Refractive Index: 1.475
• Boiling Point: 346oC
• PKA: 12.57±0.20(Predicted)
• PSA: 49.41000
• Density: 1.145 g/cm³
• LogP: -0.76860
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: 2000 g/L
• Water Solubility.: 2000 g/L
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 142.074227566
• Heavy Atom Count: 10
• Complexity: 167

Purity/Quality:

98%, ^*data from raw suppliers

1-Ethyl-2,3-dioxopiperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCNC(=O)C1=O
• Uses: 1-Ethyl-2,3-dioxopiperazine is an intermediate used in the new process for the synthesis of Piperacillin sodium. 1-Ethyl-2,3-dioxopiperazine (Piperacillin EP Impurity E; Piperacillin USP Related Compound E) is an intermediate used in the new process for the synthesis of Piperacillin sodium.

Technology Process of 1-Ethylpiperazine-2,3-dione

There total 3 articles about 1-Ethylpiperazine-2,3-dione 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: 83.21%

N-ethylethane-1,2-diamine (110-72-5) + oxalic acid diethyl ester (95-92-1) → 1-ethyl-2,3-dioxo-piperazine (59702-31-7)

Guidance literature:

With acetic acid; In methanol; at 15 - 50 ℃; for 1h; Reagent/catalyst;

Reference yield: 76.0%

→ 1-ethyl-2,3-dioxo-piperazine (59702-31-7)

Guidance literature:

Reference yield: 21.0%

6-<(+/-)-α-amino-α-(2-aminothiazol-4-yl)acetamido>penicillanic acid (85208-10-2) + 4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride (59703-00-3) → 6-<(+/-)-α-(2-aminothiazol-4-yl)-α-(4-ethyl-2,3-dioxopiperazin-1-ylcarbonylamino)acetamido>penicillanic acid (85208-19-1,85208-20-4,85280-44-0) + 1-ethyl-2,3-dioxo-piperazine (59702-31-7)

Guidance literature:

With sodium hydrogencarbonate; 1.) THF, H₂O, 0 deg C, 2.) pH=7-7.5, room temperature, 1 h;

upstream raw materials:

6-<(+/-)-α-amino-α-(2-aminothiazol-4-yl)acetamido>penicillanic acid

4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

N-ethylethane-1,2-diamine

oxalic acid diethyl ester

Downstream raw materials:

4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

piperacillin

(4-ethyl-2, 3-dioxo-piperazin-1-yl)-acetic acid

1-[4-(2-aminoethyl)benzyl]-4-ethylpiperazine-2,3-dione hydrochloride

Refernces

• 1、 Hardy, Kenneth D.,Harrington, Frank P.,Stachulski, Andrew V.. "The Chemistry of Some 2-Aminothiazol-4-ylacetic Acid Derivatives and the Synthesis of Derived Penicillins". . p. 1227 - 1236. Retrieved 2007/10/02.
• 2、 -. "Novel penicillins and cephalosporins and process for producing the same". . . Retrieved 2008/06/13.