cas 84467-85-6, N-Formyl N,N-Didesmethyl Sibutramine | Articles data ｜lookchem

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84467-85-6

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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
Han, Zhengxu,Krishnamurthy, Dhileepkumar,Pflum, Derek,Fang, Qun K.,Butler, Hal,Cameron,Wald, Stephen A.,Senanayake, Chris H.
p. 107 - 109
(2007/10/03)

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.
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(2008/06/13)

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).
Reddy, G. Om,Sarma,Chandrasekhar,Babu, J. Moses,Prasad,Raju, C.M. Haricharan
p. 488 - 492
(2013/09/08)

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.
Jeffery, James E.,Kerrigan, Frank,Miller, Thomas K.,Smith, Graham J.,Tometzki, Gerald B.
p. 2583 - 2589
(2007/10/03)

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Chemical Properties

Melting Point: 110-111°C
Boiling Point: 425.7°C at 760 mmHg
Flash Point:211.2°C
Density: 1.102g/cm³
Solubility:Chloroform (Slightly), Methanol (Slightly)
Storage Temp.:-20°C Freezer
Vapor Pressure: 1.88E-07mmHg at 25°C
PKA: 15.95±0.23(Predicted)
PSA: 32.59000
LogP: 4.76270

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