Hydrochloric Acid → HCID 68535627, compound

HRID 644219Notes

Reaction equation

HRID 644219 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[CH:22]=[CH:21][C:16]=2[C:17]([O:19]C)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[CH:22]=[CH:21][C:16]=2[C:17]([OH:19])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68530937HCID 68530937, compound

Product 1

HCID 68535627HCID 68535627, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(4-chloro-phenyl)benzoate (0.3 g 0.67 mmol) in dioxane (10 mL) and aqueous NaOH (2 g in 10 mL H2O) was heated at reflux for 4 h. The reaction was then cooled to room temperature, acidified to pH 3 with 1 N HCl, and extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo to give 0.293 g of product (100%).

Workup

  1. temperatureat reflux for 4 h
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47e26fba7c3e4361b9b8fa8b7417121d
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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