Water → N-Acetyl-N-(3-ethoxycarbonylaminophenethyl)amine

HRID 1173127Notes

Reaction equation

HRID 1173127 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)(=[O:3])[CH3:2].Cl[C:15]([O:17][CH2:18][CH3:19])=[O:16].O>N1C=CC=CC=1>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10928Ethyl chloroformateHCID 22674097N-Acetyl-N-(3-aminophenethyl)amine

Product 1

HCID 22674171N-Acetyl-N-(3-ethoxycarbonylaminophenethyl)amineYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-Acetyl-N-(3-aminophenethyl)amine (1.7 g, Production Example 29b) was dissolved in pyridine (5 ml). Under ice-cooling, ethyl chloroformate (1.4 ml) was added dropwise thereinto, followed by stirring at room temperature for one hour. Then, the mixture was ice-cooled again and water was added thereto. The mixture was extracted with ethyl acetate, and the extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, to give the title compound (2.358 g, 97%) as a yellow oil.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturecooled again
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-714c56258bdf47f3a5d4827d3a5d0379
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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