Water → Citalopram

HRID 1370026Notes

Reaction equation

HRID 1370026 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.Cl[CH2:11][C:12]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][Mg]Cl.O>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][C:14]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]2[C:12](=[CH:20][C:19]([C:21]#[N:22])=[CH:18][CH:17]=2)[CH2:11][O:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 113449102-(Chloromethyl)-4-cyanobenzoyl chlorideHCID 178418676HCID 178418676, compoundHCID 178483494HCID 178483494, compound

Product 1

HCID 2771CitalopramYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-fluoro phenylmagnesium bromide (0.7M in THF, 16 ml) was added to a cooled solution of 2-chloromethyl-4-cyano-benzoyl chloride (1,75 g) in toluene (20 ml) so that the temperature did not rise above 0° C. After 40 minutes a solution of 3-dimethylaminopropylmagnesium chloride (0,85 M in THF, 10 ml) was added so that the temperature did not rise above 2° C. The mixture was stirred for 30 minutes, and water (30 ml) was added. The pH of the mixture was adjusted to 4.5, and the phases were separated. The pH of the aqueous phase was adjusted to 8 and extracted with toluene (30 ml) and 2-propanol (10 ml). The organic phase was concentrated in vacuo to give a viscous oil (1,5 g, 56%). Spectral and analytical data were in accordance with the literature.

Workup

  1. customdid not rise above 0° C
  2. customdid not rise above 2° C
  3. customthe phases were separated
  4. extractionextracted with toluene (30 ml) and 2-propanol (10 ml)
  5. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-6c3ece7d277142959c4f831a0b2a176b
Source dataset
uspto-grants-2003_06
Patent number
US06579993B2

Reaction notes

Loading…