Phenylethanolamine → N-(2-hydroxy-2-phenylethyl)acetamide

HRID 1004483Notes

Reaction equation

HRID 1004483 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8].C(N(CC)CC)C>C(Cl)Cl>[OH:8][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:6][NH:5][C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1000PhenylethanolamineHCID 6367Acetyl chlorideHCID 8471Triethylamine

Product 1

HCID 270963N-(2-hydroxy-2-phenylethyl)acetamideYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of acetyl chloride (10 ml, 0.146 moles) in 200 ml of methylene chloride was added under nitrogen dropwise over 45 minutes to a solution of 2-amino-1-phenylethanol (20.0 g, 0.146 moles) and triethylamine (20 ml, 0.146 moles) in 300 ml of methylene chloride at ice bath temperature. After the addition the reaction was stirred at ice bath temperature for 3 hours and overnight at room temperature. The reaction was extracted with 1N HCl. The organic layer was separated and the aqueous layer was extracted with methylene chloride and then 10% methanol-methylene chloride. The organic extracts were combined, dried (MgSO4) and the solvent removed under reduced pressure to give a solid material. Recrystallization of this solid from isopropyl alcohol gave N-(2-hydroxy-2-phenyl-ethyl)-acetamide (9.0 g, 34%) as a white solid, mp 120-122° C.

Workup

  1. additionAfter the addition the reaction
  2. customovernight
  3. customat room temperature
  4. extractionThe reaction was extracted with 1N HCl
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with methylene chloride
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed under reduced pressure
  9. customto give a solid material
  10. customRecrystallization of this solid from isopropyl alcohol

Sources & evidence

ORD record
ord-4e10ccde42f94310831aed5ac8c263d9
Source dataset
uspto-grants-2000_04
Patent number
US06049006

Reaction notes

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