4-Benzyloxybenzylamine → 4-Hydroxybenzylamine

HRID 850463

Reaction equation

HRID 850463 reaction equation
C([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[C].[Pd].C1COCC1>[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 42928454-BenzyloxybenzylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 974724-HydroxybenzylamineYield 85%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium-carbon catalyst (water content 50%, 50 mg) was added to a solution of 4-benzyloxybenzylamine (530 mg, 2.485 mmol, 1.0 eq) in THF (10 ml), and the mixture was stirred for 3 hours at room temperature in a stream of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (n-hexane/ethyl acetate=1/1) to give 4-hydroxybenzylamine (260 mg, 85.0%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-cb6bd5b742c84021a56ca1cda3c9581f
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Linked notes

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