Water → Citalopram

HRID 2065996Notes

Reaction equation

HRID 2065996 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][C:7]1([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[O:15][CH2:14][C:13]2[CH:12]=[C:11]([C:16]#[N:17])[CH:10]=[CH:9][C:8]1=2)[CH3:3].Br.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[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:15][CH2:14][C:13]2[CH:12]=[C:11]([C:16]#[N:17])[CH:10]=[CH:9][C:8]1=2)[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 77995Citalopram Hydrobromide

Product 1

HCID 2771Citalopram

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of citalopram hydrobromide (200 Kg, 0.49 kmoles), in toluene (300 lit) and water (200 lit) were stirred at room temperature. The mixture was cooled to 20° C., basified with 10% NaOH solution (100 lit) to pH 9-10 and the phases separated. The aqueous layer was extracted with toluene (2×150 lit). The combined organic solutions were washed with water, dried on sodium sulphate, filtered and used for the next step.

Workup

  1. customthe phases separated
  2. extractionThe aqueous layer was extracted with toluene (2×150 lit)
  3. washThe combined organic solutions were washed with water
  4. customdried on sodium sulphate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-94a2d00f243f4901b843c7f288710df5
Source dataset
uspto-grants-2012_10
Patent number
US08288568B2

Reaction notes

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