Hydrochloric Acid → HCID 66792779, compound

HRID 535003Notes

Reaction equation

HRID 535003 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]([C:20]2[N:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([O:30]C)=[O:29])=[CH:22][CH:21]=2)=[O:19])[CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>O1CCCC1>[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]([C:20]2[N:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][CH:21]=2)=[O:19])[CH2:14][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66750858HCID 66750858, compound

Product 1

HCID 66792779HCID 66792779, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl [(6-{[4-(2-tert-butyl-4-chlorophenyl)piperazin-1-yl]carbonyl}pyridin-3-yl)oxy]acetate (Example 209, 0.25 g, 0.56 mmol) and 1 M LiOH solution (5 mL, 5.0 mmol) in tetrahydrofuran (5 mL) was stirred at 0° C. for 2 h. The reaction mixture was acidified with 1 M HCl solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.21 g, 87%) as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a124d8196ad24956927124c7026d231e
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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