Hydrogen Bromide → Citalopram Hydrobromide

HRID 1375201Notes

Reaction equation

HRID 1375201 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 Hydrobromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 7.1 g of citalopram base in 35 ml of dichloromethane a solution of 7 g of sodium metabisulphite in 25 ml of deionized water is added. The pH of the mixture is brought to 6.0 by addition of 5% aqueous ammonium hydroxide, then the organic phase is discarded, the aqueous one is brought to pH=7.0 by addition of sodium bicarbonate and extracted with 2×10 ml of toluene. The organic phases are concentrated under vacuum at 50° C. to give 6.9 g of citalopram base with purity (HPLC)=99.8% (area). These 6.9 g of citalopram base are dissolved in 30 ml of acetone and 48% HBr is added to the solution to a pH of 4÷5. The obtained solution is evaporated under vacuum and the residue is crystallized with acetone to give 5.6 g of citalopram hydrobromide with purity (HPLC)=99.4% (area) and m.p. 185÷187° C.

Workup

  1. customThe obtained solution is evaporated under vacuum
  2. customthe residue is crystallized with acetone

Sources & evidence

ORD record
ord-0afba983b97b427bb5fb104868c491fc
Source dataset
uspto-grants-2007_01
Patent number
US07166729B2

Reaction notes

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