4-Methylmorpholine → N,N-di-n-Butyl-2-benzyloxyacetamide

HRID 1635076

Reaction equation

HRID 1635076 reaction equation
CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:16]([O:23][CH2:24][C:25]([OH:27])=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:28]([NH:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH3:31]>C1COCC1.O>[CH2:28]([N:32]([CH2:33][CH2:34][CH2:35][CH3:36])[C:25](=[O:27])[CH2:24][O:23][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 8148DibutylamineHCID 62365Isobutyl chloroformateHCID 290301(Benzyloxy)acetic acid

Product 1

HCID 18675619N,N-di-n-Butyl-2-benzyloxyacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3 g of N-methylmorpholine and 4 g of isobutyl chloroformate were successively added dropwise to 5 g of 2-benzyloxyacetic acid in 50 ml of THF at −10° C. The mixture was stirred for 10 minutes and then 5 ml of di-n-butylamine and a further 3 g of N-methylmorpholine were added. After one hour, the mixture was added to 500 ml of water and extracted several times with ether. The collected organic phases were dried over magnesium sulfate and, after removal of the solvent by distillation, 7 g of an oil were isolated and were immediately employed further.

Workup

  1. waitAfter one hour
  2. extractionextracted several times with ether
  3. dry with materialThe collected organic phases were dried over magnesium sulfate
  4. customafter removal of the solvent
  5. distillationby distillation

Sources & evidence

ORD record
ord-72439baae5ef4e1f8fdc8da1bc0db42f
Source dataset
uspto-grants-2003_01
Patent number
US06509341B1

Linked notes

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