Ethyl 2-(3-formylphenoxy)acetate (III) was prepared by alkylation of 3-hydroxybenzaldehyde (I) with ethyl bromoacetate (II) in the presence of K2CO3 and KI. Reduction of aldehyde (III) with NaBH4 provided the benzyl alcohol (IV), which was further protected as the silyl ether (V) by treatment with tert-butyldimethylsilyl chloride and imidazole. Addition of methylmagnesium bromide to the ester function of (V) yielded the tertiary alcohol (VI). Condensation of the sodium alkoxide of (VI) with 3-(bromomethyl)thiophene (VII) furnished ether (VIII). After desilylation of (VIII) employing tetrabutylammonium fluoride, the resultant benzyl alcohol (IX) was treated with methanesulfonyl chloride and triethylamine to afford mesylate (X). Alkylation of amine (XI) with mesylate (X) furnished the target tertiary amine, which was finally treated with HCl in EtOAc to afford the corresponding hydrochloride salt.

Ethyl 2-(3-formylphenoxy)acetate (III) was prepared by alkylation of 3-hydroxybenzaldehyde (I) with ethyl bromoacetate (II) in the presence of K2CO3 and KI. Reduction of aldehyde (III) with NaBH4 provided the benzyl alcohol (IV), which was further protected as the silyl ether (V) by treatment with tert-butyldimethylsilyl chloride and imidazole. Addition of methylmagnesium bromide to the ester function of (V) yielded the tertiary alcohol (VI). Condensation of the sodium alkoxide of (VI) with 3-(bromomethyl)thiophene (VII) furnished ether (VIII). After desilylation of (VIII) employing tetrabutylammonium fluoride, the resultant benzyl alcohol (IX) was treated with methanesulfonyl chloride and triethylamine to afford mesylate (X). Alkylation of amine (XI) with mesylate (X) furnished the target tertiary amine, which was finally treated with HCl in EtOAc to afford the corresponding hydrochloride salt.