Hydrogen Bromide → Citalopram Hydrobromide

HRID 489491Notes

Reaction equation

HRID 489491 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 Bromide2×HCID 2771Citalopram

Product 1

HCID 77995Citalopram Hydrobromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Citalopram base (167 g) was dissolved in acetone (837 ml). Thereto was blown in a hydrobromic acid gas at 15° C.-40° C. to make the pH of the solution 3. When about 1/2 of the hydrobromic acid gas was blown in, crystals began to precipitate. The reaction mixture was stirred at 25° C.-35° C. for 1 hour, and at 0° C.-5° C. for 1 hour. The resulting crystals were filtered, washed with cold acetone (167 ml) and dried in vacuo at 50° C.-70° C. (5 Torr-30 Torr) for 3 hours to give citalopram hydrobromide crystals (162 g). The crystals had an HPLC purity of 97.3% (254 nm).

Workup

  1. customto precipitate
  2. waitat 0° C.-5° C. for 1 hour
  3. filtrationThe resulting crystals were filtered
  4. washwashed with cold acetone (167 ml)
  5. customdried in vacuo at 50° C.-70° C. (5 Torr-30 Torr) for 3 hours

Sources & evidence

ORD record
ord-937a88f3d7f74c52be7be0d872138204
Source dataset
uspto-grants-2005_12
Patent number
US06977306B2

Reaction notes

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