Tert-butyl 4-[3-(ethylamino)pyridin-2-yl]piperazine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 4-[3-(ethylamino)pyridin-2-yl]piperazine-1-carboxylate
• CAS No.: 111669-26-2
• Molecular Formula: C₁₆H₂₆N₄O₂
• Molecular Weight: 306.408
• DSSTox Substance ID: DTXSID30699143
• Wikidata: Q82629913
• Mol file: 111669-26-2.mol

Synonyms:111669-26-2;tert-butyl 4-[3-(ethylamino)pyridin-2-yl]piperazine-1-carboxylate;4-(3-ethylaminopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester;4-(3-ETHYLAMINO-PYRIDIN-2-YL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;SCHEMBL3330474;DTXSID30699143;AKOS015911521;1-Piperazinecarboxylicacid,4-[3-(ethylamino)-2-pyridinyl]-,1,1-dimethylethyl ester

Chemical Property of Tert-butyl 4-[3-(ethylamino)pyridin-2-yl]piperazine-1-carboxylate

Chemical Property:

• Boiling Point: 454.6±45.0 °C(Predicted)
• PKA: 9.76±0.30(Predicted)
• PSA: 57.70000
• Density: 1.138±0.06 g/cm3(Predicted)
• LogP: 2.64640
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 306.20557608
• Heavy Atom Count: 22
• Complexity: 362

Purity/Quality:

99%min ^*data from raw suppliers

4-(3-ETHYLAMINO-PYRIDIN-2-YL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC1=C(N=CC=C1)N2CCN(CC2)C(=O)OC(C)(C)C

Technology Process of Tert-butyl 4-[3-(ethylamino)pyridin-2-yl]piperazine-1-carboxylate

There total 4 articles about Tert-butyl 4-[3-(ethylamino)pyridin-2-yl]piperazine-1-carboxylate 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: 91.0%

1-[1,1-dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine (111669-25-1) + acetaldehyde (75-07-0,9002-91-9) → 4-(3-ethylaminopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (111669-26-2)

Guidance literature:

With sodium cyanoborohydride; In methanol; at 20 ℃; for 48h;

Reference yield:

2-Chloro-3-nitropyridine (5470-18-8,34515-82-7) → 4-(3-ethylaminopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (111669-26-2)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / acetonitrile / 3 h / Heating

2: H₂, 1.2 N aq. HCl / 10percent Pd/C / ethanol / 16 h / 2378.9 Torr

3: Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

4: sodium cyanoborohydride / acetonitrile / 48 h / Ambient temperature

With hydrogenchloride; hydrogen; sodium cyanoborohydride; potassium carbonate; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm00166a010

Reference yield:

1-(3-nitro-2-pyridinyl)piperazine (87394-48-7) → 4-(3-ethylaminopyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (111669-26-2)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂, 1.2 N aq. HCl / 10percent Pd/C / ethanol / 16 h / 2378.9 Torr

2: Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

3: sodium cyanoborohydride / acetonitrile / 48 h / Ambient temperature

With hydrogenchloride; hydrogen; sodium cyanoborohydride; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm00166a010

upstream raw materials:

1-[1,1-dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine

acetaldehyde

2-Chloro-3-nitropyridine

1-(3-amino-pyridin-2-yl)-piperazine

Downstream raw materials:

4-[3-(Ethylamino)-2-pyridinyl]-piperazine

Refernces

• 1、 Jacobsen, E. Jon,McCall, John M.,Ayer, Donald E.,VanDoornik, Fred J.,Palmer, John R.,et al.. "Novel 21-Aminosteroids That Inhibit Iron-Dependent Lipid Peroxidation and Protect against Central Nervous System Trauma". . p. 1145 - 1151. Retrieved 2007/10/02.