Phenethylamine → N-(2-phenylethyl)acetamide

HRID 1461795Notes

Reaction equation

HRID 1461795 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>C1(C)C=CC=CC=1>[C:10]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 7918Acetic Anhydride

Product 1

HCID 70143N-(2-phenylethyl)acetamideYield 95.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

121.18 g of phenethylamine is dissolved in 450 ml of toluene in a 2 l three-necked flask. 102.09 g (95 ml) of acetic anhydride is added dropwise over a half hour period the temperature rises to 110° . After the addition is completed, the reaction solution temperature is maintained at approximately 95° C. The solvent is removed in vacuo and the residual oil was distilled under high vacuum (bp 160°-165° C./1mm) to afford 156.6 g of a white crystalline solid. The product exhibited NMR peaks (CDCl3, δ) at 7.35, 3.45, 2.80, and 1.90.

Workup

  1. customrises to 110°
  2. additionAfter the addition
  3. customThe solvent is removed in vacuo
  4. distillationthe residual oil was distilled under high vacuum (bp 160°-165° C./1mm)

Sources & evidence

ORD record
ord-0323a088f1054a9586ccb8596f59fb36
Source dataset
uspto-grants-1991_12
Patent number
US05077407

Reaction notes

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