Water → N,O-Diacetyl-4-hydroxyamphetamine
Reaction equation
Br.[OH:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][CH:8]([NH2:10])[CH3:9])=[CH:5][CH:4]=1.O.[C:14](OC(=O)C)(=[O:16])[CH3:15].[OH-].[Na+].[C:23](OCC)(=[O:25])[CH3:24]>>[C:14]([O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]([NH:10][C:23](=[O:25])[CH3:24])[CH3:9])=[CH:11][CH:12]=1)(=[O:16])[CH3:15]Participants
Conditions
- Temperature
- 5 °C
Procedure
In a 1-l. flask, flushed with nitrogen and provided with a stirrer, thermometer, two dropping funnels, and a nitrogen inlet tube was placed a solution of 46.4 g. (0.2 moles) of rac. 4-hydroxy-alpha-methylphenethylamine hydrobromide in 100 ml. of water. The flask was cooled in an ice bath, and when the temperature reached 5° C., 40 ml. of acetic anhydride (0.395 moles) and 440 ml. of 2N NaOH were added simultaneously from the two dropping funnels at approximately equivalent rates, maintaining the temperature below 5° C. An oil gradually separated during the addition, and the mixture was stirred for another 4 hours at 5° C., then allowed to come to room temperature overnight. The oil that had solidified to a mass of crystals was recovered by filtration. After washing with water the solid was dried in vacuo over KOH and CaCl2. Yield, 32 g. of mp. 92°-93.5°. An analytical sample was obtained by recrystallization from ethyl acetate-- 30°-60° C. petroleum ether; mp. 97.5° - 99° C.
Workup
- customflask, flushed with nitrogen
- customprovided with a stirrer
- temperatureThe flask was cooled in an ice bath
- customreached 5° C.
- temperaturemaintaining the temperature below 5° C
- customAn oil gradually separated during the addition
- waitto come to room temperature overnight
- filtrationwas recovered by filtration
- washAfter washing with water the solid
- dry with materialwas dried in vacuo over KOH and CaCl2
- customYield
Sources & evidence
- ORD record
- ord-aeea13e126b14c5081a852b339a079e0
- Source dataset
- uspto-grants-1977_08
- Patent number
- US04041076
Reaction notes
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