Hydrogen Bromide → Citalopram Hydrobromide

HRID 496867Notes

Reaction equation

HRID 496867 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].[BrH:25]>CC(C)=O>[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].[BrH:25]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 2771Citalopram

Product 1

HCID 77995Citalopram HydrobromideYield 83.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution (94.1 kg including citalopram 51.8 kg) of citalopram in acetone produced in Example 30 was added to acetone (163.4 kg) and hydrogen bromide (13.2 kg) was blown in over 3 hr at 25-35° C. After aging for 3 hr, the mixture was cooled to about 5° C. and aged at 0-5° C. for three more hours. The crystals were collected by filtration and washed with acetone (40.9 kg) cooled to 0-5° C. The crystals were dried under reduced pressure at 30-50° C. to give citalopram hydrobromide (54.9 kg, yield 83.7%).

Workup

  1. customwas blown in over 3 hr at 25-35° C
  2. customaged at 0-5° C. for three more hours
  3. filtrationThe crystals were collected by filtration
  4. washwashed with acetone (40.9 kg)
  5. temperaturecooled to 0-5° C
  6. customThe crystals were dried under reduced pressure at 30-50° C.

Sources & evidence

ORD record
ord-384975218759430ea6f34cd0a0a1f3eb
Source dataset
uspto-grants-2005_09
Patent number
US06946564B2

Reaction notes

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