Hydrochloric Acid → Hydroxyamfetamine

HRID 6729

Reaction equation

HRID 6729 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH3:10])=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:18].[Na+].Cl>CO>[NH2:18][CH:9]([CH3:10])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 3651HydroxyamfetamineYield 56.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-hydroxyphenylacetone (0.5 g, Avocado, U.K.) and ammonium acetate (2.54 g, Aldrich, U.S.A.) in 10 mL methanol was added 0.17 g of sodium cyanoborohydride (Aldrich, U.S.A.). After stirring for 72 h at rt, concentrated hydrochloric acid was added dropwise until the solution reached pH 2. The solvent was evaporated and the resulting residue was dissolved in water, then extracted 3 times with diethyl ether. The aqueous layer was neutralized to pH 8 by the addition of potassium hydroxide and extracted with diethyl ether. The basic ether layer was dried over sodium sulfate and the solvent was removed in vacuo to give 0.23 g of 4-(2-amino-propyl)-phenol.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting residue was dissolved in water
  3. extractionextracted 3 times with diethyl ether
  4. additionThe aqueous layer was neutralized to pH 8 by the addition of potassium hydroxide
  5. extractionextracted with diethyl ether
  6. dry with materialThe basic ether layer was dried over sodium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-66b12eb350804cde8d3d3a98c42becda
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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