N-Formyl N,N-Didesmethyl Sibutramine

Base Information

• Chemical Name: N-Formyl N,N-Didesmethyl Sibutramine
• CAS No.: 84467-85-6
• Molecular Formula: C16H22ClNO
• Molecular Weight: 279.80498
• Hs Code.: 29242990
• UNII: P623ZR3N4K
• DSSTox Substance ID: DTXSID80517661
• Nikkaji Number: J1.347.042A
• Wikidata: Q27286273
• Mol file: 84467-85-6.mol

Synonyms:N-Formyl N,N-Didesmethyl Sibutramine;84467-85-6;N-[1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl]formamide;N-Formyl-desmethyl-sibutramine;P623ZR3N4K;N-{1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutyl}formamide;Formamide, N-(1-(1-(4-chlorophenyl)cyclobutyl)-3-methylbutyl)-;Formamide, N-[1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl]-;SCHEMBL2644;UNII-P623ZR3N4K;DTXSID80517661;FT-0668823;Q27286273;Formamide,N-[1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl]-

Chemical Property of N-Formyl N,N-Didesmethyl Sibutramine

Chemical Property:

• Vapor Pressure: 1.88E-07mmHg at 25°C
• Melting Point: 110-111°C
• Boiling Point: 425.7°C at 760 mmHg
• PKA: 15.95±0.23(Predicted)
• Flash Point: 211.2°C
• PSA: 32.59000
• Density: 1.102g/cm³
• LogP: 4.76270
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 279.1389920
• Heavy Atom Count: 19
• Complexity: 293

Purity/Quality:

99.90% ^*data from raw suppliers

N-Formyl N,N-Didesmethyl Sibutramine| ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)NC=O
• Uses: An intermediate of a Sibutramine metabolite, a serotonin and noradrenaline reuptake inhibitor (SNR). Decreases calorie intake and increases energy expenditure.

Technology Process of N-Formyl N,N-Didesmethyl Sibutramine

There total 7 articles about N-Formyl N,N-Didesmethyl Sibutramine 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%

Methyl formate (107-31-3) + didesmethylsibutramine (106650-56-0,84467-54-9) → N-{1-[1-(4-chlorophenylcyclobutyl)]-3-methylbuty}formamide (84467-85-6)

Guidance literature:

for 16h; Heating;

DOI:10.1039/p19960002583

Reference yield: 39.0%

formamide (77287-34-4,77287-35-5,60100-09-6) + 1-[1-(4-chloro-phenyl)cyclobutyl]-3-methyl-butan-1-one (186521-85-7) → N-{1-[1-(4-chlorophenylcyclobutyl)]-3-methylbuty}formamide (84467-85-6)

Guidance literature:

In formic acid; at 160 - 180 ℃; for 24.5h;

DOI:10.1021/op980093t

Reference yield:

p-chlorobenzyl cyanide (140-53-4) → N-{1-[1-(4-chlorophenylcyclobutyl)]-3-methylbuty}formamide (84467-85-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / KOH / diethyl ether; dimethylsulfoxide / 1 h / 20 - 25 °C

3: 30 percent / HCO₂H / 17 h / 180 °C

With potassium hydroxide; formic acid; In diethyl ether; dimethyl sulfoxide;

DOI:10.1039/p19960002583

upstream raw materials:

Methyl formate

didesmethylsibutramine

formamide

1-[1-(4-chloro-phenyl)cyclobutyl]-3-methyl-butan-1-one

Downstream raw materials:

sibutramine hydrochloride

(-)-Desmethylsibutramine hydrochloride

(+)-Desmethylsibutramine hydrochloride

(+/-)-Desmethylsibutramine hydrochloride

Refernces

• 1、 -. "Aryl-substituted cyclobutylalkylamines for treating obesity". . . Retrieved 2008/06/13.
• 2、 Jeffery, James E.,Kerrigan, Frank,Miller, Thomas K.,Smith, Graham J.,Tometzki, Gerald B.. "Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites". . p. 2583 - 2589. Retrieved 2007/10/03.