Hydroxyamfetamine → Acetamide, N-[2-(4-hydroxyphenyl)-1-methylethyl]-

HRID 76159

Reaction equation

HRID 76159 reaction equation
[NH2:1][CH:2]([CH3:11])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18]>O.C(#N)C>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH:2]([NH:1][C:17](=[O:19])[CH3:18])[CH3:11])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 3651HydroxyamfetamineHCID 7918Acetic AnhydrideHCID 516892Sodium Bicarbonate

Product 1

HCID 584229Acetamide, N-[2-(4-hydroxyphenyl)-1-methylethyl]-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

1.88 g (10.0 mmol) 4-(2-amino-propyl)-phenol*HCl and 1.80 g (21.0 mmol) NaHCO3 are combined in 50 mL water and cooled down to 0° C. 0.95 mL (10.0 mmol) acetic anhydride, dissolved in 50 mL ACN, are dropped into the mixture over a period of 1.5 h. The reaction mixture is stirred at r.t. for 72 h. The ACN is evaporated in vacuo and the aq. residue is acidified with HCl (1N). The mixture is extracted several times with EtOAc. The organic layers are combined, dried with Na2SO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, DCM/MeOH 95/5).

Workup

  1. additionare dropped into the mixture over a period of 1.5 h
  2. customThe ACN is evaporated in vacuo
  3. extractionThe mixture is extracted several times with EtOAc
  4. dry with materialdried with Na2SO4
  5. customthe solvent is removed in vacuo
  6. customThe crude product is purified by column chromatography (silica gel, DCM/MeOH 95/5)

Sources & evidence

ORD record
ord-b0e8197c822641c39eb4e1d339b0eda3
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Linked notes

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