1-(6-Acetylamino-3-nitro-2-pyridyl)-4-ethoxycarbonylpiperazine

Base Information

• Chemical Name: 1-(6-Acetylamino-3-nitro-2-pyridyl)-4-ethoxycarbonylpiperazine
• CAS No.: 75167-23-6
• Molecular Formula: C14H19N5O5
• Molecular Weight: 337.335
• DSSTox Substance ID: DTXSID10388700
• Nikkaji Number: J93.679K
• Mol file: 75167-23-6.mol

Synonyms:NIOSH/TK7862500;TK78625000;1-(6-Acetylamino-3-nitro-2-pyridyl)-4-ethoxycarbonylpiperazine;4-(6-Acetamido-3-nitro-2-pyridyl)-1-piperazineacetic acid ethyl ester;1-Piperazineacetic acid, 4-(6-acetamido-3-nitro-2-pyridyl)-, ethyl ester;75167-23-6;SCHEMBL10967689;DTXSID10388700;ethyl 4-(6-acetamido-3-nitropyridin-2-yl)piperazine-1-carboxylate;4-(6-Acetylamino-3-nitro-2-pyridyl)-1-piperazinecarboxylic acid ethyl ester

Chemical Property of 1-(6-Acetylamino-3-nitro-2-pyridyl)-4-ethoxycarbonylpiperazine

Chemical Property:

• PSA: 124.08000
• LogP: 2.40230
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 337.13861872
• Heavy Atom Count: 24
• Complexity: 475

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1CCN(CC1)C2=C(C=CC(=N2)NC(=O)C)[N+](=O)[O-]

Technology Process of 1-(6-Acetylamino-3-nitro-2-pyridyl)-4-ethoxycarbonylpiperazine

There total 2 articles about 1-(6-Acetylamino-3-nitro-2-pyridyl)-4-ethoxycarbonylpiperazine 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: 95.0%

acetic anhydride (108-24-7) + 4-(6-Amino-3-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester (75167-22-5) → 6-acetylamino-2-(4-ethoxycarbonyl-1-piperazinyl)-3-nitropyridine (75167-23-6)

Guidance literature:

In acetic acid; at 90 ℃; for 0.5h;

DOI:10.1002/jhet.5570210309

Reference yield:

4-(6-chloro-3-nitro-2-pyridinyl)-1-piperazinecarboxylic acid,ethyl ester (75167-21-4) → 6-acetylamino-2-(4-ethoxycarbonyl-1-piperazinyl)-3-nitropyridine (75167-23-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 54.6 percent / 13percent ammonia / ethanol / 15 h / 100 - 110 °C / autoclave

2: 95 percent / acetic acid / 0.5 h / 90 °C

With ammonium hydroxide; In ethanol; acetic acid;

DOI:10.1002/jhet.5570210309

Reference yield:

6-acetylamino-2-(4-ethoxycarbonyl-1-piperazinyl)-3-nitropyridine (75167-23-6) → enoxacine (74011-58-8)

Guidance literature:

Multi-step reaction with 9 steps

1: zinc powder, acetic acid / ethanol / 0.17 h / Heating

2: 42percent tetrafluoroboric acid, sodium nitrite / ethanol; H₂O / 0.17 h / -7 - -4 °C

3: 82.3 percent / toluene / 4 h / Heating

4: 10percent HCl / methanol / 2 h / Heating

5: ethanol / 2 h / Heating

6: 75.8 percent / Dowtherm A / 0.22 h / 248 - 249 °C

7: 1.) potassium carbonate / 1.) DMF, 100 deg C, 30 min; 2.) 100 deg C, 3 h

8: 72.9 percent / 15percent HCl / ethanol / 0.25 h / Heating

9: 87 percent / 10percent NaOH / ethanol / 4 h / Heating

With hydrogenchloride; sodium hydroxide; tetrafluoroboric acid; diphenyl ether-biphenyl eutectic; potassium carbonate; acetic acid; zinc; sodium nitrite; In methanol; ethanol; water; toluene;

DOI:10.1002/jhet.5570210309

upstream raw materials:

acetic anhydride

4-(6-Amino-3-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester

4-(6-chloro-3-nitro-2-pyridinyl)-1-piperazinecarboxylic acid,ethyl ester

Downstream raw materials:

4-(6-Acetylamino-3-amino-pyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester

enoxacine

6-amino-2-(4-ethoxycarbonyl-1-piperazinyl)-3-fluoropyridine