Triethylamine → 2-[Methyl(phenyl)amino]ethyl propionate

HRID 2184077Notes

Reaction equation

HRID 2184077 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH2:20][CH3:21]>C(Cl)Cl.CCOC(C)=O>[C:19]([O:5][CH2:4][CH2:3][N:2]([CH3:1])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:22])[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 623402-(N-Methylanilino)ethanol

Product 1

HCID 224756282-[Methyl(phenyl)amino]ethyl propionateYield 102.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[methyl(phenyl)amino]ethanol (500 mg, 3.3 mmol) in CH2Cl2 (17 mL) was added triethylamine (1.4 mL, 9.9 mmol) followed by propionyl chloride (0.4 mL, 5.0 mmol). After stirring at ambient temperature over 18 hours, the reaction mixture was diluted with EtOAc and washed several times with brine. The organic layer was dried (Na2SO4) and concentrated to afford the title compound (700 mg, quantitative yield). MS (ES+) m/z 208 (MH+).

Workup

  1. washwashed several times with brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4bc9ef07affa4fecb6616b941794a704
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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