Hydrochloric Acid → HCID 49764240, compound

HRID 534972Notes

Reaction equation

HRID 534972 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:24])[C:19]([O:21]CC)=[O:20])[CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>CCO>[C:1]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[N:12]1[CH2:13][CH2:14][N:15]([C:18](=[O:24])[C:19]([OH:21])=[O:20])[CH2:16][CH2:17]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66750875HCID 66750875, compound

Product 1

HCID 49764240HCID 49764240, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl [4-(2-tert-butyl-4-chlorophenyl)piperazin-1-yl](oxo)acetate (Example 179, 0.45 g, 1.28 mmol) and 1 M LiOH (3.8 mL) in EtOH (15 mL) was stirred at room temperature for 1 h. The reaction mixture was acidified with 1 M HCl, concentrated under reduced pressure, and partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting white solid was triturated with diisopropyl ether to give the title compound (0.29 g) as a white solid: mp 154-155° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting white solid was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-af36c938b0154071a02e868b4ee1eaa1
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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