5-Benzylfuran-2-carbaldehyde → 5-(Phenylmethyl)-2-furanmethanamine

HRID 2080254

Reaction equation

HRID 2080254 reaction equation
[CH2:1]([C:8]1[O:12][C:11]([CH:13]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:15].CO>[Ni]>[CH2:1]([C:8]1[O:12][C:11]([CH2:13][NH2:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 124185375-Benzylfuran-2-carbaldehydeHCID 21705897Ammonia methanol

Product 1

HCID 231306205-(Phenylmethyl)-2-furanmethanamineYield 65.8%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

7N Ammonia/methanol(40 mL) and Raney nickel(3 g) were added to 5-benzyl-furan-2-carbaldehyde described in Preparation Example 39 (2.5 g, 13 mmol), and the solution was stirred for 22 hours under hydrogen atmosphere at room temperature. After removing the catalyst by filtering through Celite pad, the solvent was evaporated in vacuo and C-(5-benzyl-furan-2-yl)methylamine (1.6 g, 8.6 mmol, 65.8%) was obtained.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtering through Celite pad
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fa9049e0f9524da9bf4ee48ab4ee6885
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Linked notes

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