Methanol → HCID 89585116, compound

HRID 1501182Notes

Reaction equation

HRID 1501182 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH:12]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].O1CCCC1.CO.[OH-].[Li+]>O>[CH3:1][C:2]1[CH:11]=[C:10]([CH:12]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 89585118HCID 89585118, compound

Product 1

HCID 89585116HCID 89585116, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-methyl-4-(1-(piperidin-1-yl)ethyl)benzoate (283 mg, 1.1 mmol) in the mixture solution of tetrahydrofuran:methanol:water=3:1:1 (10 mL) was added lithium hydroxide (100 mg, 4.2 mmol). The mixture was stirred at room temperature for 2 hours. The suspension was concentrated in vacuo and quenched with hydrochloride acid aqueous (1N, 5 mL). To the residue was added water (50 mL). The mixture was extracted with dichloromethane (2*50 mL). The combined organic phase was separated, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give the product 2-methyl-4-(1-(piperidin-1-yl)ethyl)benzoic acid as pale solid (247 mg, 89%).

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. customquenched with hydrochloride acid aqueous (1N, 5 mL)
  3. additionTo the residue was added water (50 mL)
  4. extractionThe mixture was extracted with dichloromethane (2*50 mL)
  5. customThe combined organic phase was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4e77e949bb4047adb45e07d44b648580
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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