Benzaldehyde → 4-(2-(Benzylamino)ethyl)phenol

HRID 601594Notes

Reaction equation

HRID 601594 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[CH2:11]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 5610Tyramine

Product 1

HCID 30425724-(2-(Benzylamino)ethyl)phenolYield 519.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine tyramine (3.0 g, 3.3 mmol), benzaldehyde (3.0, 2.2 mmol), 3 Å molecular sieves (5 g), and ethanol (3 mL) and stir overnight at room temperature. Filter off the sieves then add sodium borohydride (2.5 g) to the reaction at 0° C. then stirred at room temperature overnight. Concentrate on a rotary evaporator, take up residue in water, and then extract with dichloromethane (3×100 mL). Dry the dichloromethane extracts over sodium chloride/magnesium sulfate, filter, then concentrate on a rotary evaporator to yield 4.3 g of the crude product. The crude product is purified by flash column chromatography on silica gel eluting with 10% conc. ammonium hydroxide in ethanol and chloroform to yield 4-(2-benzylamino-ethyl)-phenol (2.6 g): 1H NMR (DMSO-D6, 300.00 MHz): 9.17 (s, 1H), 7.31 (m, 5H), 6.99 (d, 2H, J=8.4 Hz), 6.67 (d, 2H, J=8.8 Hz), 3.70 (s, 2H), 2.64 (m, 4H), 2.11 (s, 1H).

Workup

  1. filtrationFilter off the sieves
  2. customadd sodium borohydride (2.5 g) to the reaction at 0° C.
  3. concentrationConcentrate on a rotary evaporator
  4. extractionextract with dichloromethane (3×100 mL)
  5. dry with materialDry the dichloromethane
  6. filtrationfilter
  7. concentrationconcentrate on a rotary evaporator
  8. customto yield 4.3 g of the crude product
  9. customThe crude product is purified by flash column chromatography on silica gel eluting with 10% conc. ammonium hydroxide in ethanol and chloroform

Sources & evidence

ORD record
ord-c2e4d56af90b4c4f918cf1745c78baba
Source dataset
uspto-grants-2011_03
Patent number
US07902372B2

Reaction notes

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