Water → N-[2-(4-Methoxyphenyl)propyl]acetamide

HRID 1709275Notes

Reaction equation

HRID 1709275 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH3:4].O.C(=O)(O)[O-].[Na+].[C:19](Cl)(=[O:21])[CH3:20]>C(OCC)(=O)C>[C:19]([NH:1][CH2:2][CH:3]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[CH3:4])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 2026252-(4-Methoxyphenyl)propan-1-amineHCID 516892Sodium Bicarbonate

Product 1

HCID 14579484N-[2-(4-Methoxyphenyl)propyl]acetamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 19.8 g of 1-amino-2-(4-methoxyphenyl)propane, 200 ml of ethyl acetate, 200 ml of water and 84 g of sodium bicarbonate is cooled at 5° to 10° C. under stirring, and 18.8 g of acetyl chloride in 100 ml of ethyl acetate are added dropwise thereto at the same temperature. After the reaction, the ethyl acetate layer is separated therefrom, washed, dried and then condensed to dryness under reduced pressure. 24.8 g of 1-acetylamino-2-(4-methoxyphenyl)propane are obtained as oil.

Workup

  1. temperatureis cooled at 5° to 10° C.
  2. customAfter the reaction
  3. customthe ethyl acetate layer is separated
  4. washwashed
  5. customdried
  6. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-22b1727281c84c45b1f4c781668f8386
Source dataset
uspto-grants-1990_08
Patent number
US04948810

Reaction notes

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