2-Methoxy-3-methyl-5-(3,6-dioxo-4-methyl-2-piperazinylmethyl)benzaldehyde

Base Information

• Chemical Name: 2-Methoxy-3-methyl-5-(3,6-dioxo-4-methyl-2-piperazinylmethyl)benzaldehyde
• CAS No.: 221146-78-7
• Molecular Formula: C₁₅H₁₈N₂O₄
• Molecular Weight: 290.319
• DSSTox Substance ID: DTXSID501143678
• Nikkaji Number: J1.349.100C
• Mol file: 221146-78-7.mol

Synonyms:DTXSID501143678;2-Methoxy-3-methyl-5-(3,6-dioxo-4-methyl-2-piperazinylmethyl)benzaldehyde;2-Methoxy-3-methyl-5-[(4-methyl-3,6-dioxo-2-piperazinyl)methyl]benzaldehyde;221146-78-7

Chemical Property of 2-Methoxy-3-methyl-5-(3,6-dioxo-4-methyl-2-piperazinylmethyl)benzaldehyde

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 290.12665706
• Heavy Atom Count: 21
• Complexity: 426

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1OC)C=O)CC2C(=O)N(CC(=O)N2)C

Technology Process of 2-Methoxy-3-methyl-5-(3,6-dioxo-4-methyl-2-piperazinylmethyl)benzaldehyde

There total 1 articles about 2-Methoxy-3-methyl-5-(3,6-dioxo-4-methyl-2-piperazinylmethyl)benzaldehyde 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: 77.0%

Dichloromethyl methyl ether (4885-02-3) + 3-(4-methoxy-3-methylphenylmethyl)-1-methyl-2,5-piperazinedione (146515-59-5) → 3-(3-formyl-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione (221146-78-7)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 25 ℃; for 1h;

Reference yield: 75.0%

3-(3-formyl-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione (221146-78-7) → 3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione (221146-79-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; at 25 ℃; for 8h;

Reference yield:

3-(3-formyl-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione (221146-78-7) → 2-(2-bromo-5-hydroxy-4-methoxy-3-methyl-benzyl)-6-hydroxy-4-methyl-3-oxo-piperazine-1-carboxylic acid isopropyl ester (310904-06-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / m-CPBA; TFA / CH₂Cl₂ / 8 h / 20 °C

2: 91.2 percent / K₂CO₃ / dimethylformamide / 24 h / 80 °C

3: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 43 h / 20 °C

4: 93.3 percent / H₂ / 20 percent Pd(OH)2/C / ethanol / 1 h / 760 Torr

5: 89.2 percent / Br₂ / CCl₄; CH₂Cl₂ / 1 h / 0 °C

6: LiAl(OtBu)3H / tetrahydrofuran / 1 h / 0 °C

With dmap; hydrogen; bromine; potassium carbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Baeyer-Villiger oxidation;

DOI:10.1248/cpb.48.1549

upstream raw materials:

Dichloromethyl methyl ether

3-(4-methoxy-3-methylphenylmethyl)-1-methyl-2,5-piperazinedione

Downstream raw materials:

3-(3-hydroxy-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione

3-(2-bromo-5-hydroxy-4-methoxy-3-methylphenylmethyl)-1-methyl-2,5-piperazinedione

3-(3-benzyloxy-4-methoxy-5-methylphenylmethyl)-1-methyl-2,5-piperazinedione

2-(2-bromo-5-hydroxy-4-methoxy-3-methyl-benzyl)-6-hydroxy-4-methyl-3-oxo-piperazine-1-carboxylic acid isopropyl ester