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

HRID 1005684Notes

Reaction equation

HRID 1005684 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

In pyridine (5 ml) was dissolved 1.7 g of N-acetyl-N-(3-aminophenethyl)amine (Preparation Example 29), followed by dropwise addition of ethyl chloroformate (1.4 ml) under ice-cooling. After stirring at room temperature for 1 hour, the mixture was ice-cooled again. Water was added thereto, followed by extracting with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give the title compound (2.358 g, 97%) as a yellow oil.

Workup

  1. temperaturecooling
  2. temperaturecooled again
  3. extractionby extracting 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-d50f8460846d43158c9a1f4863c7c1ca
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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