(R)-4-benzyl-2-hydroxymethylpiperazine

Base Information

• Chemical Name: (R)-4-benzyl-2-hydroxymethylpiperazine
• CAS No.: 149715-46-8
• Molecular Formula: C12H18N2O
• Molecular Weight: 206.288
• Hs Code.: 2933599590
• DSSTox Substance ID: DTXSID10428014
• Wikidata: Q72442731
• Mol file: 149715-46-8.mol

Synonyms:(R)-4-benzyl-2-hydroxymethylpiperazine;149715-46-8;[(2R)-4-benzylpiperazin-2-yl]methanol;DTXSID10428014;ZFA71546;MFCD11113046;AKOS015909782;A3290;CS-0057696

Chemical Property of (R)-4-benzyl-2-hydroxymethylpiperazine

Chemical Property:

• Vapor Pressure: 0.000154mmHg at 25°C
• Refractive Index: 1.551
• Boiling Point: 318.1 °C at 760 mmHg
• PKA: 14.97±0.10(Predicted)
• Flash Point: 146.2 °C
• PSA: 35.50000
• Density: 1.083 g/cm³
• LogP: 0.71940
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 206.141913202
• Heavy Atom Count: 15
• Complexity: 181

Purity/Quality:

98%min ^*data from raw suppliers

(R)-4-Benzyl-2-hydroxymethylpiperazine 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC(N1)CO)CC2=CC=CC=C2
• Isomeric SMILES: C1CN(C[C@@H](N1)CO)CC2=CC=CC=C2

Technology Process of (R)-4-benzyl-2-hydroxymethylpiperazine

There total 7 articles about (R)-4-benzyl-2-hydroxymethylpiperazine 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%

(S)-3-(hydroxymethyl)-1-(phenylmethyl)-2,5-piperazinedione (149648-97-5) → (R)-4-(phenylmethyl)-2-piperazinemethanol (149715-46-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1.5h; Heating;

DOI:10.1021/jm00067a004

Reference yield: 82.0%

(R)-4-Benzyl-piperazine-2-carboxylic acid (137442-19-4) → (R)-4-(phenylmethyl)-2-piperazinemethanol (149715-46-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(99)01031-X

Reference yield:

N-benzyl-N-(tert-butoxycarbonyl)glycine (76315-01-0) → (R)-4-(phenylmethyl)-2-piperazinemethanol (149715-46-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, pentafluorophenol, 2.) Et₃N / 1.) dichloromethane, RT, 3 h, 2.) dichloromethane, RT, 20 h

2: 1.) SOCl₂, 2.) aq. NH₃ / 1.) methanol, RT, 2 h, 2.) methanol

3: 91 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

With ammonium hydroxide; lithium aluminium tetrahydride; thionyl chloride; 2,3,4,5,6-pentafluorophenol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran;

DOI:10.1021/jm00067a004

upstream raw materials:

(S)-3-(hydroxymethyl)-1-(phenylmethyl)-2,5-piperazinedione

(R)-4-Benzyl-piperazine-2-carboxylic acid

benzyl chloride

N-benzyl-N-(tert-butoxycarbonyl)glycine

Downstream raw materials:

(R)-piperazin-2-ylmethanol

(R)-tert-butyl4-benzyl-2-(hydroxymethyl)piperazine-1-carboxylate

(R)-2-(hydroxymethyl)piperazine-1-carboxylic acid tert-butyl ester

(R)-methyl 4-<(3,4-dichlorophenyl)acetyl>-3-(hydroxymethyl)-1-piperazinecarboxylate

Refernces

• 1、 -. "Fluorine-substituted monocarbazole derivative as well as preparation method and application thereof (by machine translation)". Paragraph 0206-0210. . Retrieved 2020/06/20.
• 2、 Naylor,Judd,Lloyd,Scopes,Hayes,Birch. "A potent new class of κ-receptor agonist: 4-Substituted 1-(arylacetyl)- 2-[(dialkylamino)methyl]piperazines". . p. 2075 - 2083. Retrieved 2007/10/02.