Donepezil benzyl chloride is a piperidine-based impurity derived from the parent drug donepezil, featuring a benzyl chloride substituent at the 5-position of the piperidine ring. The structure incorporates an aromatic benzene ring, a tertiary amine, and a chloromethyl linkage, which distinguishes it from the parent compound by the absence of the terminal ester and the presence of a benzyl chloride moiety. This compound arises as a synthetic byproduct during donepezil manufacturing via nucleophilic substitution reactions involving benzyl chloride reagents. It serves as a critical HPLC reference standard for quantifying process-related impurities in donepezil active pharmaceutical ingredients.
On RequestCOC1=C(C=C2C(=C1)CC(C2=O)CC3CC[N+](CC3)(CC4=CC=CC=C4)CC5=CC=CC=C5)OC.[Cl-]
InChI=1S/C31H36NO3.ClH/c1-34-29-19-26-18-27(31(33)28(26)20-30(29)35-2)17-23-13-15-32(16-14-23,21-24-9-5-3-6-10-24)22-25-11-7-4-8-12-25;/h3-12,19-20,23,27H,13-18,21-22H2,1-2H3;1H/q+1;/p-1
AEVRPYIRFJXZNZ-UHFFFAOYSA-M