Ammonium Chloride → 4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol

Participants

Reaction Conditions

Reaction Steps

To a suspension of Sodium thiomethoxide (49.2 g, 0.702 mol, 5 eq) in DMF (140 ml) was added {[4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-yl]methyl}dimethylamine (35 g, 0.140 mol) and the resulting mixture was heated to 130° C. Once complete, allowed to cool to ambient temperature and saturated aqueous NH4Cl (525 ml) was added. The resultant was extracted with EtOAc (3×500 ml), dried over MgSO4, filtered and concentrated in vacuo at 35° C. to provide 4-(4-dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (intermediate 3) as a yellow solid (35.7 g, 108%) containing residual DMF and EtOAc.

Provenance & Evidence