Hydrochloric Acid → Efletirizine

HRID 1249671Notes

Reaction equation

HRID 1249671 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][O:19][CH2:20][C:21](N)=[O:22])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[Na].[OH-:32].[Na+].Cl>O.C(O)C>[CH:8]1[C:7]([CH:10]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][O:19][CH2:20][C:21]([OH:32])=[O:22])[CH2:15][CH2:16]2)[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)=[CH:6][CH:5]=[C:4]([F:3])[CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 18328707HCID 18328707, compound

Product 1

HCID 66003Efletirizine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a round-bottomed flask fitted with a mechanical stirrer, a Nitrogen inlet and a condenser, 30 g (0.065 mole) of 2-[4-[bis(4-fluorophenyl)methyl]-1-piperazinyl]ethoxyacetamide dihydrochloride are added to a mixture of 325 ml of ethanol, 130 ml of a 1 N aqueous sodium hydroxyde solution and 62 ml of a 6.3 N aqueous sodium hydroxide solution. The mixture is heated under reflux and under a Nitrogen atmosphere for 1.5 hours. The reaction mixture is then cooled down to room temperature and its pH is adjusted to 5 with 78 ml of a 5 N aqueous hydrochloric acid solution. Water is added, and ethanol is evaporated off under vacuum using a rotary evaporator. The resulting aqueous phase is extracted with dichloromethane. The organic phase is dried over anhydrous sodium sulphate and evaporated to dryness to give 25 g of crude efletirizine as an amorphous solid, 5 g of which are recrystallized in acetonitrile.

Workup

  1. customIn a round-bottomed flask fitted with a mechanical stirrer, a Nitrogen inlet and a condenser
  2. temperatureThe mixture is heated
  3. temperatureunder reflux and under a Nitrogen atmosphere for 1.5 hours
  4. customethanol is evaporated off under vacuum
  5. customa rotary evaporator
  6. extractionThe resulting aqueous phase is extracted with dichloromethane
  7. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-0229c57c880f4696a6fc0765df608ffa
Source dataset
uspto-grants-2002_01
Patent number
US06335331B1

Reaction notes

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