84467-85-6

Basic information

• Product Name: N-Formyl N,N-Didesmethyl Sibutramine
• Synonyms: N-Formyl N,N-Didesmethyl Sibutramine ;N-(1-(1-(4-Chlorophenyl)cyclobutyl)-3-methylbutyl)formamide;ForMaMide, N-[1-[1-(4- chlorophenyl)cyclobutyl]-3- Methylbutyl]-
• CAS NO: 84467-85-6
• Molecular Formula: C₁₆H₂₂ClNO
• Molecular Weight: 279.80498
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 84467-85-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 110-111°C
• Boiling Point: 425.7°C at 760 mmHg
• Flash Point: 211.2°C
• Appearance: /
• Density: 1.102g/cm³
• Vapor Pressure: 1.88E-07mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.95±0.23(Predicted)
• CAS DataBase Reference: N-Formyl N,N-Didesmethyl Sibutramine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Formyl N,N-Didesmethyl Sibutramine(84467-85-6)
• EPA Substance Registry System: N-Formyl N,N-Didesmethyl Sibutramine(84467-85-6)

Safety Data

• Hazardous Substances Data: 84467-85-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

An intermediate of a Sibutramine metabolite, a serotonin and noradrenaline reuptake inhibitor (SNR). Decreases calorie intake and increases energy expenditure.

InChI:InChI=1/C16H22ClNO/c1-12(2)10-15(18-11-19)16(8-3-9-16)13-4-6-14(17)7-5-13/h4-7,11-12,15H,3,8-10H2,1-2H3,(H,18,19)

Upstream product

• 107-31-3 Methyl formate 
• 106650-56-0 didesmethylsibutramine 
• 77287-34-4 formamide 
• 186521-85-7 1-[1-(4-chloro-phenyl)cyclobutyl]-3-methyl-butan-1-one 
• 64-18-6 formic acid 
• 28049-61-8 1-(4-chlorophenyl)cyclobutanecarbonitrile 
• 421558-88-5 1-[1-(4-chloro-phenyl)-cyclobutyl]-3-methyl-butylideneamine 
• 140-53-4 p-chlorobenzyl cyanide 

Downstream Products

• 106650-56-0 didesmethylsibutramine 
• 84467-94-7 (+/-)-Desmethylsibutramine hydrochloride 
• 84467-94-7 (+)-Desmethylsibutramine hydrochloride 
• 84485-00-7 sibutramine hydrochloride 
• 84467-94-7 (-)-Desmethylsibutramine hydrochloride 

Relevant articles and documents

First practical synthesis of enantiomerically pure (R)- and (S)-desmethylsibutramine (DMS) and unambiguous determination of their absolute configuration by single-crystal X-ray analysis

A practical synthesis of enantiomerically pure (R)-desmethylsibutramine [(R)-DMS] and (S)-desmethylsibutramine [(S)-DMS] is outlined along with an improved synthesis of racemic desmethylsibutramine. This route was used for kilo-scale production of enantio

A study and identification of potential by-products of sibutramine

In the synthesis and process development of sibutramine (9), the isolation and characterization of two potential by-products namely heptane dinitriles (4a-b) and bis-cyclobutyl alkylamine (10) have been studied. The key steps in the synthesis of sibutramine which have contributed to the formation of above by-products are cycloalkylation of 4-chlorophenyl acetonitrile (1) and tandem Grignard reduction on 1-(4-chlorophenyl)cyclobutyl carbonitrile (3).