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

HRID 601577Notes

Reaction equation

HRID 601577 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.[BH4-].[Na+]>CO>[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

5

Reactant 3

HCID 240BenzaldehydeHCID 5610TyramineHCID 4311764Sodium borohydride

Product 1

HCID 30425724-(2-(Benzylamino)ethyl)phenolYield 39.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Combine tyramine (5 g, 36.5 mmol), benzaldehyde (9.9 g, 45.6 mmol), 3 Å molecular sieves (10 g), and methanol (200 mL) and stir overnight at room temperature. Cool to 5° C. then add sodium borohydride (5.5 g, 146 mmol) to the reaction. Stir for 2 hours then concentrate on a rotary evaporator. Dilute in methanol, filter, then concentrate on a rotary evaporator. The residue was taken up in 1N hydrochloric acid and washed with diethyl ether. The aqueous layer was basified then extracted with ethyl acetate (2×100 mL. The ethyl acetate extracts were combined, dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield 4-(2-Benzylamino-ethyl)-phenol (3.3 g) 1H NMR (CDCl3, 300.00 MHz): 9.14 (s, 1H), 7.35-7.20 (m, 5H), 7.01-6.96 (m, 2H), 6.69-6.64 (m, 2H), 5.19 (s, 1H), 3.73 (s, 2H), 2.72-2.60 (m, 4H).

Workup

  1. concentrationthen concentrate on a rotary evaporator
  2. additionDilute in methanol
  3. filtrationfilter
  4. concentrationconcentrate on a rotary evaporator
  5. washwashed with diethyl ether
  6. extractionThe aqueous layer was basified then extracted with ethyl acetate (2×100 mL
  7. dry with materialdried over sodium chloride/magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-02661b9212454df6942a8473d8b1561e
Source dataset
uspto-grants-2011_03
Patent number
US07902372B2

Reaction notes

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