Hydrochloric Acid → 2-(4-Methoxy-2-methylphenyl)-ethylamine hydrochloride

HRID 2386898Notes

Reaction equation

HRID 2386898 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[C:5]([CH3:12])[CH:4]=1.[ClH:13].[H][H]>C(O)C.[Pd]>[ClH:13].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[C:5]([CH3:12])[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 38010242-(4-Methoxy-2-methylphenyl)acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 670320342-(4-Methoxy-2-methylphenyl)-ethylamine hydrochlorideYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

4-Methoxy-2-methylphenylacetonitrile (3.0 g, 18.6 mmol) was dissolved in 2B ethanol (65 mL). To the solution was added con. HCl (2.4 mL) and 10% Pd/C (300 mg). The suspension was deaerated in a 500 mL Parr hydrogenation bottle and then pressurized with 55 psi H2, and shaken. After 20 h, the reaction was recharged with hydrogen and 10% Pd/C. After a total of 96 h, the reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The off-white solid residue was recrystallized from isopropanol and collected by suction filtration to afford 1.86 g (50% yield) 2-(4-methoxy-2-methylphenyl)-ethylamine hydrochloride as a white solid, melting point (M.P.) 220-222° C. (gradual softening and discoloration from 104-220° C.). The filtrate was concentrated in vacuo and the residue was washed with ethyl acetate and filtered, providing an additional 1.34 g for a total yield of 3.2 g (85% yield). GC/MS: m/z 165; 1H NMR (DMSO) 8.25 (bs, 3H), 7.09 (d, 1H), 6.75 (m, 2H), 3.71 (s, 3H), 2.87 (m, 4H), 2.27 (s, 3H).

Workup

  1. additionTo the solution was added con
  2. filtrationAfter a total of 96 h, the reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe off-white solid residue was recrystallized from isopropanol
  5. filtrationcollected by suction filtration

Sources & evidence

ORD record
ord-657fe4badfea4b7ea0caf97763de478f
Source dataset
uspto-grants-2012_09
Patent number
US08268843B2

Reaction notes

Loading…