N-benzyl-2-chloro-N-(2-hydroxyethyl)acetamide → 4-Benzylmorpholin-3-one

HRID 30320Notes

Reaction equation

HRID 30320 reaction equation
[CH2:1]([N:8]([CH2:13][CH2:14][OH:15])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[CH2:1]([N:8]1[CH2:13][CH2:14][O:15][CH2:10][C:9]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3732022N-benzyl-2-chloro-N-(2-hydroxyethyl)acetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 122940874-Benzylmorpholin-3-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Conditions

Temperature
27.5 °C

Procedure

A solution of N-benzyl-N-(2-hydroxyethyl)chloroacetamide (627.7 g, 2.76 mol) in tert-butanol (0.9 L) is stirred under nitrogen while warming to 25-30° C. Potassium tert-butoxide (2.897 L of a 1M solution in tert-butanol, 2.90 mol, 1.05 eq) is added over 2 hours. The reaction mixture is then stirred at room temperature for 90 minutes. Ice-cold water (6 L) is added and the resultant cloudy solution extracted with ethyl acetate. The combined organic layers are washed with brine, dried over magnesium sulphate and evaporated in vacuo to give a light brown oil (441 g, 84%), which is used in the next stage without further purification; MW 191.23; C11H13NO2; 1H NMR (CDCl3): 7.29-7.40 (5H, m), 4.67 (2H, s), 4.28 (2H, s), 3.87 (2H, t, 5 Hz), 3.31 (2H, t, 5 Hz); LCMS: (12 min method) m/z 192 [M+H]+RT 1.00 min.

Workup

  1. extractionthe resultant cloudy solution extracted with ethyl acetate
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-852f6bcd053b43b4a8976206c35db6c4
Source dataset
uspto-grants-2008_09
Patent number
US07423037B2

Reaction notes

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