Benzylethanolamine → 4-benzylmorpholin-2-one

HRID 517657Notes

Reaction equation

HRID 517657 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=[O:13].[K+].[K+].[CH2:18](OC(=O)CBr)[C:19]1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:19][CH2:18][O:11][C:10](=[O:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4348BenzylethanolamineHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetate

Product 1

HCID 2273624-benzylmorpholin-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of Compound 2 (355.8 mg, 2.353 mmol) and K2CO3 (565 mg, 4.09 mmol) in anhydrous CHCl3 (12 mL) at 0° C. was dropwise added Benzyl-2-bromoacetate (540 mg, 2.36 mmol) over 0.5 h. The reaction mixture was gradually warmed to room temperature and stirred for 36 h. The resulting reaction mixture was filtered while washing with CH2Cl2, and the filtrate was concentrated to give Compound 3. 1H NMR (CDCl3) δ 2.7 (t, 2H), 3.3 (s, 2H), 3.6 (s, 2H) 4.4 (t, 2H), 7.2-7.4 (m, 5H); 13C NMR (CDCl3) δ 48.49, 55.64, 61.59, 68.69, 127.67, 128.48, 128.87, 136.04, 167.37. HRMS (Positive ion FAB) Calcd for C11H13NO2 [M+H]+ m/z 192.0900. Found: [M+H]+ m/z 192.1032.

Workup

  1. customover 0.5 h
  2. customThe resulting reaction mixture
  3. filtrationwas filtered
  4. washwhile washing with CH2Cl2
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9e0c43557ab74a64b36ccbe423cce0f1
Source dataset
uspto-grants-2015_08
Patent number
US09115094B2

Reaction notes

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