Hydrogen Bromide → Citalopram

HRID 1370023

Reaction equation

HRID 1370023 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][Mg]Cl.Cl[CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:14]#[N:15].Br>COCCOC>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][C:19]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:18]2[C:11](=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=2)[CH2:10][O:27]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 99434343-Chloromethyl-4-(4-fluoro-benzoyl)-benzonitrileHCID 178483494HCID 178483494, compound

Product 1

HCID 2771CitalopramYield 75%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of freshly prepared 3-dimethylaminopropylmagnesium chloride (0.6 M in THF, 7.6 ml) was added to a cooled solution of 3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile (0.5 g) in ethylene glycol dimethyl ether (4 ml) so that the temperature did not raise above −40° C. The mixture was stirred for 30 minutes at −15° C. and 100 minutes at room temperature before 0.5N hydrobromic acid was added to adjust the pH to 10. The phases were separated and the aqueous phase was extracted twice with toluene (25 ml). The combined organic phases were dried over sodium sulfate, filtered and dried in vacuo to give a viscous oil (0.44 g, 75%). Spectral and analytical data were in accordance with the literature.

Workup

  1. temperaturedid not raise above −40° C
  2. additionwas added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted twice with toluene (25 ml)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7afe70c7f1834bb4aa22e4a0665a4e14
Source dataset
uspto-grants-2003_06
Patent number
US06579993B2

Linked notes

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