Water → Citalopram

HRID 353605

Reaction equation

HRID 353605 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].O.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1>[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

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 99434343-Chloromethyl-4-(4-fluoro-benzoyl)-benzonitrileHCID 178483494HCID 178483494, compound

Product 1

HCID 2771CitalopramYield 95%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-dimethylaminopropylmagnesium chloride (1.2M in THF, 84 ml) was added to a cooled solution of 3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile (25.0 g) in a mixture of toluene (175 ml) and THF (50 ml) so that the temperature did not raise above −5° C. The mixture was stirred for 2 hours at 0° C. before water (100 ml) and saturated NH4Cl solution were added to adjust the pH to 9. The phases were separated and the aqueous phase was extracted twice with toluene (200 ml). The combined organic phases were washed with water (200 ml) and concentrated in vacuo to give a viscous oil (28.0 g, 95%). Spectral and analytical data were in accordance with the literature.

Workup

  1. temperaturedid not raise above −5° C
  2. additionwere added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted twice with toluene (200 ml)
  5. washThe combined organic phases were washed with water (200 ml)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fe10d7afa064bd0b37a5530ba77ebcb
Source dataset
uspto-grants-2004_06
Patent number
US06753433B2

Linked notes

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