Oxalic Acid → N-Desmethyl Citalopram Oxalate

Participants

Reaction Steps

A solution of 1-[3-(N-methyl-ammonium)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile (0.70 g, 2.24 mmol) and formaldehyde (0.5 mL, 6.7 mmol, 37% aqueous solution) in 98% formic acid (5 mL) was refluxed for 4 h. After cooling, 4M HCI (2 mL) was added and the resulting mixture was evaporated. 1M NaOH (50 mL) was added to the residue and extracted with Et2O (3×100 mL). The organic extract was washed with brine, dried and evaporated. The oxalate salt was isolated from acetone (0.22 g, 30%). DSC (open chamber), Tonset=157.73, Tpeak=160.80. The NMR-spectra were identical with those obtained from citalopram oxalate prepared in example 6. Anal. (C20H21N2O, C2H2O4, ¼ H2O) calcd. C: 63.06; H: 5.67; N: 6.69. Found C: 63.24; H: 5.65; N: 6.62.

Provenance & Evidence