2-Chloro-N,N-dimethylethylamine → 4-{2-[4-(2-Dimethylamino-ethoxy)-phenyl]-4-hydroxymethyl-4-methyl-cyclohex-1-enyl}-phenol

Participants

Reaction Conditions

Reaction Steps

To a solution of (1-methyl-3,4-di(4-hydroxy-phenyl)-cyclohex-3-enyl)-methanol (30 mg, 1 eq.) in DMF (1 mL) was added NaH (10 mg, 1 eq.), and the reaction mixture was then stirred for 2 h at 25° C. To the reaction mixture was then added (2-chloro-ethyl)-dimethyl-amine (12 mg, 1 eq) and the mixture stirred for 16 hours. The reaction mixture was then partitioned between H2O/ethyl acetate (5 mL/5 mL). The organic layer was separated, dried over MgSO4, concentrated and purified HPLC (20%˜80% CH3CN/H2O with 0.1% TFA) to yield 4-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-4-hydroxymethyl-4-methyl-cyclohex-1-enyl}-phenol.

Provenance & Evidence