84467-85-6

Usage

Uses

Used in Pharmaceutical Industry:
N-Formyl N,N-Didesmethyl Sibutramine is used as an intermediate in the synthesis of Sibutramine for its pharmacological effects. It plays a role in the metabolism of Sibutramine, which is utilized as an appetite suppressant and weight loss medication. N-Formyl N,N-Didesmethyl Sibutramine helps decrease calorie intake and increase energy expenditure, making it a valuable component in the development of weight management therapies.

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

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

Relevant academic research and scientific papers

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

Aryl-substituted cyclobutylalkylamines for treating obesity

PCT No. PCT/EP96/02239 Sec. 371 Date Apr. 27, 1998 Sec. 102(e) Date Apr. 27, 1998 PCT Filed May 24, 1996 PCT Pub. No. WO96/38134 PCT Pub. Date Dec. 5, 1996Use of aryl-substituted cyclobutylalkylamines and their pharmaceutically suitable salts for treating obesity and its accompanying disorders are disclosed.

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).

Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites

Synthetic routes to N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine (sibutramine) 1 and its demethylated and hydroxylated human metabolites N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methyibutyl}-N-methylamine2, 1-[1-(4-chiorophenyl)cyclobutyl]-3-methylbutylamine 3, 4-amino-4-[1-(4-chlorophenyl)cyclobutyl]-2-methylbutan-1-ol 4 and c-3-(1-amino-3-methylbutyl)-3-(4-chlorophenyl)cyclobutan-r-1-ol 5a are described. Key steps are tandem Grignard-reduction reactions on 1-(4-chlorophenyl)cyclobutanecarbonitrile 7 and its 3-(tetrahydropyran-2-yloxy)-substituted analogue 14 and a convenient one-pot conversion of 4-chlorophenylacetonitrile 6 into the 3-hydroxycyclobutanecarbonitrile 13.