4-chloro-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]-N-methylbenzamide

Base Information

• Chemical Name: 4-chloro-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]-N-methylbenzamide
• CAS No.: 67579-11-7
• Molecular Formula: C₁₆H₂₃ClN₂O
• Molecular Weight: 294.824
• DSSTox Substance ID: DTXSID501342692
• Mol file: 67579-11-7.mol

Synonyms:67579-11-7;4-chloro-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]-N-methylbenzamide;trans-4-chloro-N-[2-(dimethylamino)cyclohexyl]-N-methyl-benzamide;U-48520;DTXSID501342692;rel-4-Chloro-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]-N-methylbenzamide

Chemical Property of 4-chloro-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]-N-methylbenzamide

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 294.1498911
• Heavy Atom Count: 20
• Complexity: 326

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)C1CCCCC1N(C)C(=O)C2=CC=C(C=C2)Cl
• Isomeric SMILES: CN(C)[C@@H]1CCCC[C@H]1N(C)C(=O)C2=CC=C(C=C2)Cl

Technology Process of 4-chloro-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]-N-methylbenzamide

There total 8 articles about 4-chloro-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]-N-methylbenzamide 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:

trans-N-<2-(dimethylamino)cyclohexyl>formamide (67198-27-0) → trans-p-chloro-N-<2-(dimethylamino)cyclohexyl>-N-methylbenzamide (67579-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / LAH / diethyl ether / 17 h / Heating

2: 1 g / triethylamine / diethyl ether / 17 h / Ambient temperature

With lithium aluminium tetrahydride; triethylamine; In diethyl ether;

DOI:10.1021/jm00150a017

Reference yield:

4-chloro-benzoyl chloride (122-01-0) + trans-N,N-dimethyl-N-methyl-1,2-cyclohexanediamine (67198-26-9) → trans-p-chloro-N-<2-(dimethylamino)cyclohexyl>-N-methylbenzamide (67579-11-7)

Guidance literature:

With triethylamine; In diethyl ether; for 17h; Ambient temperature;

DOI:10.1021/jm00150a017

Reference yield:

trans-2-(N,N-dimethylamino)cyclohexanol (21651-78-5,15910-74-4) → trans-p-chloro-N-<2-(dimethylamino)cyclohexyl>-N-methylbenzamide (67579-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) NaH, THF, (ii) MeSO₂Cl, (iii) /BRN= 606221/

2: perchloric acid; hydrogen / palladium on activated charcoal / ethanol / 22 h / 2677.7 Torr

3: triethylamine / diethyl ether

With perchloric acid; hydrogen; triethylamine; palladium on activated charcoal; In diethyl ether; ethanol;

upstream raw materials:

(1R,2R)‐N,N,N'‐trimethyl‐1,2‐diaminocyclohexane

4-chloro-benzoyl chloride

trans-N,N-dimethyl-N-methyl-1,2-cyclohexanediamine

trans-N-<2-(dimethylamino)cyclohexyl>formamide