2-Amino-5-chloro-N-[1-(phenylmethyl)-4-piperidinyl]benzamide

Base Information

• Chemical Name: 2-Amino-5-chloro-N-[1-(phenylmethyl)-4-piperidinyl]benzamide
• CAS No.: 83425-17-6
• Molecular Formula: C₁₉H₂₂ClN₃O
• Molecular Weight: 343.856
• DSSTox Substance ID: DTXSID001185716
• Mol file: 83425-17-6.mol

Synonyms:2-Amino-5-chloro-N-[1-(phenylmethyl)-4-piperidinyl]benzamide;DTXSID001185716;83425-17-6

Chemical Property of 2-Amino-5-chloro-N-[1-(phenylmethyl)-4-piperidinyl]benzamide

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 343.1451400
• Heavy Atom Count: 24
• Complexity: 405

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CN(CCC1NC(=O)C2=C(C=CC(=C2)Cl)N)CC3=CC=CC=C3

Technology Process of 2-Amino-5-chloro-N-[1-(phenylmethyl)-4-piperidinyl]benzamide

There total 1 articles about 2-Amino-5-chloro-N-[1-(phenylmethyl)-4-piperidinyl]benzamide 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: 47.5%

5-Chloroisatoic anhydride (4743-17-3) + 4-amino-1-benzylpiperidine (50541-93-0) → 1-benzyl-4-(2-amino-5-chlorobenzoylamino)piperidine (83425-17-6)

Guidance literature:

With TEA; In 1,4-dioxane; for 2h; Heating;

DOI:10.1248/cpb.34.1907

Reference yield: 88.7%

chloroformic acid ethyl ester (541-41-3) + 1-benzyl-4-(2-amino-5-chlorobenzoylamino)piperidine (83425-17-6) → 1-ethoxycarbonyl-4-(2-ethoxycarbonylamino-5-chlorobenzoylamino)piperidine (104260-18-6)

Guidance literature:

at 93 ℃; for 3h;

DOI:10.1248/cpb.34.1907

Reference yield:

1-benzyl-4-(2-amino-5-chlorobenzoylamino)piperidine (83425-17-6) → 6-Chloro-3-[1-(2-oxo-2-phenyl-ethyl)-piperidin-4-yl]-1H-quinazoline-2,4-dione (104260-16-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 88.7 percent / 3 h / 93 °C

2: 76.4 percent / KOH / ethanol / 3 h / Heating

3: 70.4 percent / 47percent aq. HBr / 8 h / Heating

4: TEA / methanol / Ambient temperature

With potassium hydroxide; TEA; hydrogen bromide; In methanol; ethanol;

DOI:10.1248/cpb.34.1907

upstream raw materials:

5-Chloroisatoic anhydride

4-amino-1-benzylpiperidine

Downstream raw materials:

1-ethoxycarbonyl-4-(2-ethoxycarbonylamino-5-chlorobenzoylamino)piperidine

6-Chloro-3-[1-(2-oxo-2-phenyl-ethyl)-piperidin-4-yl]-1H-quinazoline-2,4-dione

6-Chloro-3-[1-(2-hydroxy-2-phenyl-ethyl)-piperidin-4-yl]-1H-quinazoline-2,4-dione

6-Chloro-3-{1-[2-(3,4-dimethoxy-phenyl)-2-oxo-ethyl]-piperidin-4-yl}-1H-quinazoline-2,4-dione