(2R,5R)-2,5-dimethylpiperazine

Base Information

• Chemical Name: (2R,5R)-2,5-dimethylpiperazine
• CAS No.: 155836-53-6
• Molecular Formula: C6H14N2
• Molecular Weight: 114.191
• UNII: IWX4GF7P8E
• DSSTox Substance ID: DTXSID30878850
• Nikkaji Number: J110.471C
• Wikidata: Q72471462
• Mol file: 155836-53-6.mol

Synonyms:(2R,5R)-2,5-dimethylpiperazine;6284-84-0;(2R,5R)-rel-2,5-Dimethylpiperazine;155836-53-6;(2R,5R)-2,5-DIMETHYL-PIPERAZINE;IWX4GF7P8E;(-)-(2R,5R)-2,5-dimethylpiperazine;Piperazine, 2,5-dimethyl-, (2R,5R)-;2,5-Dimethylpiperazine, (2R,5R)-;Piperazine, 2,5-dimethyl-, (2R-cis)-;Piperazine, 2,5-dimethyl-, cis-;starbld0045736;Dimethyl-2,5-piperazin;UNII-IWX4GF7P8E;cis-2,5-Dimethyl-piperazin;SCHEMBL235447;2alpha,5alpha-Dimethylpiperazine;DTXSID30878850;NSMWYRLQHIXVAP-PHDIDXHHSA-N;AKOS006291518;CS-0454344;A856207

Chemical Property of (2R,5R)-2,5-dimethylpiperazine

Chemical Property:

• Melting Point: 165.9℃
• Flash Point: 58.3℃
• PSA: 24.06000
• Density: 0.824
• LogP: 0.61380
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 114.115698455
• Heavy Atom Count: 8
• Complexity: 62.9

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CNC(CN1)C
• Isomeric SMILES: C[C@@H]1CN[C@@H](CN1)C

Technology Process of (2R,5R)-2,5-dimethylpiperazine

There total 5 articles about (2R,5R)-2,5-dimethylpiperazine 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: 74.0%

(3R,6R)-3,6-dimethylpiperazine-2,5-dione (23927-13-1,5845-62-5) → (-)-(2R,5R)-2,5-dimethylpiperazine (155836-53-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2017.04.079

Reference yield:

Boc?D-Ala?D-Ala?OMe → (-)-(2R,5R)-2,5-dimethylpiperazine (155836-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

1.2: 26 h / 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 70 °C

With lithium aluminium tetrahydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

Reference yield:

Z-Ala-Ala-OMe (22221-78-9) → (-)-(2R,5R)-2,5-dimethylpiperazine (155836-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂/Pd-C

2: BH₃*THF / Heating

With palladium on activated charcoal; borane-THF; hydrogen;

DOI:10.1016/S0040-4039(00)84626-2

upstream raw materials:

(3R,6R)-3,6-dimethylpiperazine-2,5-dione

Z-Ala-Ala-OMe

Downstream raw materials:

C₅₈H₆₂N₆O₈S₂

C₅₁H₅₇N₅O₈S

N,N-Bis-[4-((2S,5S)-2,5-dimethyl-piperazine-1-carbonyl)-benzyl]-4-methyl-benzenesulfonamide

Refernces

• 1、 Zhu, Long-Qing,Fan, Xiao-Hong,Li, Jun-Fang,Chen, Jin-Hong,Liang, Yan,Hu, Xiao-Ling,Ma, Shu-Meng,Hao, Xiang-Yong,Shi, Tao,Wang, Zhen. "Discovery of a novel inhibitor of nitric oxide production with potential therapeutic effect on acute inflammation". supporting information. . Retrieved 2021/05/26.
• 2、 -. "Synthesis method for nitro group-containing natural product chrysamides B and diastereoisomer-compound thereof". Paragraph 0032; 0033. . Retrieved 2018/11/22.