Hydrochloric Acid → Cetirizine impurity B 2HCl

HRID 1926674Notes

Reaction equation

HRID 1926674 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[ClH:29]>O1CCOCC1>[ClH:1].[ClH:29].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]([OH:18])=[O:17])[CH2:13][CH2:14]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 68926919HCID 68926919, compound

Product 1

HCID 68928581Cetirizine impurity B 2HClYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)acetate (1.0 g, 2 mmol) in dioxane (10 mL) was added 4N HCl solution in 1,4-dioxane (20 mL, 549 mmol) followed by concentrated HCl (1.0 mL, 27 mmol). The reaction was stirred at 50° C. for 6 h and concentrated under vacuum. The crude product was triturated with EtOAc or diethyl ether, filtered, and dried to give the title compound (0.8 g, 77% yield). MS (ESI, pos. ion) m/z: 345.1 (M+1-2HCl).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe crude product was triturated with EtOAc or diethyl ether
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-efb16846793941a7bc330ee5613c65bc
Source dataset
uspto-grants-2012_05
Patent number
US08183244B2

Reaction notes

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