Patent ID: 8093428

Claim:
A process for preparing a quaternary ammonium chloride salt compound of Formula (I): wherein A is carbonyl, thiocarbonyl or sulfonyl; X is a bond or —CH═CH—; R 1 is selected from aryl and C 5 -C 15 cycloalkyl, wherein aryl in R 1 is optionally substituted with one or more lower alkyl, —(CH 2 ) n —CF 3 , lower alkoxy, alkoxycarbonyl, cyano, halogen or phenyl optionally substituted by lower alkyl, —(CH 2 ) n —CF 3 , lower alkoxy, alkoxycarbonyl, cyano or halogen, and wherein C 5 -C 15 cycloalkyl in R 1 is optionally substituted with one or more lower alkyl, —(CH 2 ) n —CF 3 , lower alkoxy, aryl, halogen-substituted aryl, alkoxycarbonyl, cyano or halogen; n is 0, 1, 2, 3 or 4; Y is a bond or —CH 2 —; X 2 is —(CH 2 ) m —, wherein m is 1 or 2; R 2 is —N + (R 4 R 5 )—ZR 3 ; Z is —(CH 2 ) p — wherein p is 0, 1 or 2; R 3 is selected from aryl and C 5 -C 15 cycloalkyl, wherein aryl in R 3 is optionally substituted with one or more lower alkyl, —(CH 2 ) n —CF 3 , lower alkoxy, aryl, halogen-substituted aryl, alkoxycarbonyl, cyano or halogen, and wherein C 5 -C 15 cycloalkyl in R 3 is optionally substituted with one or more lower alkyl, —(CH 2 ) n —CF 3 , lower alkoxy, aryl, halogen-substituted aryl, alkoxycarbonyl, cyano or halogen, and R 4 and R 5 are each individually lower alkyl or lower alkenyl; comprising the steps: Step A. reacting a Compound A1 hydrochloride salt with an aldehyde or ketone Compound A2 to provide a Compound A3: Step B. reacting Compound A3 in the presence of a metallation reagent to provide a Compound A4: Step C. reacting Compound A4 with a Compound A5 (wherein Q represents a leaving group) to provide a Compound A6: Step D. reacting Compound A6 with a chlorinated alkyl Compound C1 to provide the Compound A9, representative of the Compound of Formula (I):