Ethanolamine → 2-(Benzyloxy)ethanamine

HRID 2301600Notes

Reaction equation

HRID 2301600 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[H-].[Na+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([O:2][CH2:1][CH2:3][NH2:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 7503Benzyl ChlorideHCID 24758Sodium hydride

Product 1

HCID 5338682-(Benzyloxy)ethanamineYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethanolamine (5 g, 81.8 mmol) in 100 mL of dried THF was added 60% NaH (3.27 g, 81.8mmol) at room temperature. The mixture was heated to reflux for 30min, then benzyl chloride (9.32 g, 73.6 mmol) was added. The resulting mixture was refluxed for 3 hours. The mixture was concentrated, the residue was diluted with 1 N aq. HCl, extracted with dichloromethane. The aqueous layer was adjusted to pH>14 with 10% aq. NaOH, extracted with dichloromethane. The organic was dried over MgSO4, concentrated to give desired product (10.11 g, 82%). 1H NMR (CDCl3): δ 7.34 (m, 5H), 4.54 (s, 2H), 3.54 (t, 2H), 2.93 (t, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30min
  3. temperatureThe resulting mixture was refluxed for 3 hours
  4. concentrationThe mixture was concentrated
  5. additionthe residue was diluted with 1 N aq. HCl
  6. extractionextracted with dichloromethane
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic was dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-72475dc8810c4bd69388317a5a8f84c0
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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