Ethyl Acetate → 5-(Dimethylamino)pentanoic Acid

HRID 1478964Notes

Reaction equation

HRID 1478964 reaction equation
C(OCC1C=[C:13]([N:15]([CH3:17])[CH3:16])[CH:12]=[CH:11]C=1)(=O)CCCC.[C:18]([O:21]CC)(=[O:20])[CH3:19]>[Pd]>[CH3:16][N:15]([CH3:17])[CH2:13][CH2:12][CH2:11][CH2:19][C:18]([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 666320695-(Dimethylamino)benzyl pentanoate

Product 1

HCID 140170205-(Dimethylamino)pentanoic AcidYield 60.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

To a solution of 5-(dimethylamino)benzyl pentanoate (0.79 g, 33.6 mmol) in anhydrous ethyl acetate (20 mL) under nitrogen at room temperature was added 10% palladium on carbon (250 mg). The solution was stirred vigorously under a hydrogen atmosphere. After 16 hours additional palladium on carbon (100 mg) was added to encourage the reaction, and at 24 hours hydrogen gas was bubbled through the solution. At 40 hours the solution was filtered through celite and concentrated in vacuo to dryness to afford the product as a yellow oil (295 mg, 60.4%).

Workup

  1. customthe reaction
  2. customat 24 hours hydrogen gas was bubbled through the solution
  3. filtrationAt 40 hours the solution was filtered through celite and
  4. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-f94610c438c8482b8352bc090eb258d3
Source dataset
uspto-grants-2016_08
Patent number
US09404127B2

Reaction notes

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