Back to results
US 6,713,626 B2Granted
Process for synthesizing N-aryl piperazines with chiral N′-1-[benzoyl(2-pyridyl)amino]-2-propane substitution
AssigneeWyeth
InventorsGregg Brian Feigelson, Joseph Zeldis, Ivo Jirkovsky
Life of this patent
Estimating the term…
Abstract
A process for formation of N-aryl piperazines with chiral N′-1-[benzoyl(2-pyridyl)amino]-2-propane side-chains having the structure shown in formula below, and for making intermediate compounds therefor. In this process, chirality is introduced at the piperazine ring formation step and 2-aminopyridyl substitution is incorporated via displacement. The resulting N,N′ disubstituted piperazines act on the central nervous system at 5HT receptors.
Claims12
A process for preparing a compound of formula VII
- wherein
- R is C1-C3 alkyl,
- Y represents a moiety selected from the group consisting of C1-C6 alkoxy, C1-C6 alkyl, C3-C7 cycloalkyl and C3-C7 cycloalkoxy, and
- Ar is 2,3-dihydro-benzodioxin-5-yl, or phenyl optionally substituted with up to three substituents independently selected from halogen, methoxy, halomethyl, dihalomethyl and trihalomethyl,
- said process comprising the following steps:
- a) reacting a compound of formula III with a chiral 2-amino-1-(C3-C5)alkanol in a polar aprotic solvent to form a compound of formula IV
- wherein L represents a leaving group selected from the group consisting of Cl, Br, mesylate, triflate and tosylate, and * indicates a chiral center;
- b) converting the compound of formula IV to a compound of formula V
- wherein X is Cl or Br;
- and,
- c) treating the compound of formula V with a compound of formula VI in an aprotic solvent
- wherein M is an alkali metal.
9 more elements
Dependencies are inferred from the claim text.