Sodium Cyanide → Citalopram

Participants

Reaction Conditions

Reaction Steps

5-Amino-1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran (18 g, 0.06 mole) is dissolved in water (100 ml) and H2SO4(8 ml). NaNO2(4.1 g, 0.06 mole) is dissolved in water (20 ml) and added dropwise below 5° C. The diazotised solution is stirred for 0.5 hour at 0-5° C. pH is brought to 6.5 by adding a saturated solution of Na2CO3. This solution is added to a mixture of water (100 ml) and toluene (120 ml) containing CuCN(6 g, 0.067 mole) and NaCN (10 g, 0.2 mole) at 50-60C°. Stirring is continued for 0.5 hour. The phases are separated and the aqueous phase is further extracted with toluene (100 ml). The combined organic phase is washed with NaCN(10% aq., 2×50 ml). The solvent is removed in vacuo and the residue is chromatograhed on silica gel (ethyl acetate: n-heptane: triethylamine; 85:10:5 ) to give the title compound (6 g, 32%) as an oil.

Provenance & Evidence