Oxalic Acid → N-Desmethyl Citalopram Oxalate

HRID 1885028Notes

Reaction equation

HRID 1885028 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][C@@:7]1([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:11][CH2:10][C:9]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:8]1=2)C.[C:25]([OH:30])([C:27]([OH:29])=[O:28])=[O:26].O=C(C(=O)O)O>O>[C:27]([OH:29])(=[O:28])[C:25]([OH:30])=[O:26].[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:7]2([CH2:6][CH2:5][CH2:4][NH:2][CH3:1])[C:8]3[C:9](=[CH:12][C:13]([C:16]#[N:17])=[CH:14][CH:15]=3)[CH2:10][O:11]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 146571Escitalopram Oxalate

Product 1

HCID 12371057N-Desmethyl Citalopram Oxalate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-[3-(N-methyl-ammonium)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran-carbonitrile (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, 4 M HCI (2 mL) was added and the resulting mixture was evaporated. 1 M 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 2. 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.

Sources & evidence

ORD record
ord-bb919d120054465881ad9a6af0a7782e
Source dataset
uspto-grants-2004_07
Patent number
US06768011B2

Reaction notes

Loading…