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

HRID 131182Notes

Reaction equation

HRID 131182 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) was 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) was added over 2 hours. The reaction mixture was then stirred at room temperature for 90 minutes. Ice-cold water (6 l) was added and the resultant cloudy solution extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulphate and evaporated in vacuo to give a light brown oil (441 g, 84%), which was 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 were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-887e1f95d97349a0a0a594fae613453f
Source dataset
uspto-grants-2008_06
Patent number
US07384941B2

Reaction notes

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