Ethanol → 2-(3-Methoxyphenyl)-2-propanamine

HRID 852632Notes

Reaction equation

HRID 852632 reaction equation
C(OC(=O)[NH:10][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1)([CH3:13])[CH3:12])C1C=CC=CC=1.CCO>[Pd].O>[CH3:21][O:20][C:16]1[CH:15]=[C:14]([C:11]([NH2:10])([CH3:12])[CH3:13])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 67264266Benzyl [1-(3-methoxyphenyl)-1-methylethyl]carbamate

Product 1

HCID 139113102-(3-Methoxyphenyl)-2-propanamineYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with [1-(3-methoxy-phenyl)-1-methyl-ethyl]-carbamic acid benzyl ester (D100) (1 g, 3.34 mmol, 1 equiv), 10% palladium on charcoal (50% wet, 100 mg, 10% w/w), NH4COOH (2.1 g, 33 mmol, 10 equiv), EtOH (40 ml) and H2O (8 ml). The resulting mixture was stirred at 80° C. for 2 h, cooled to room temperature and the catalyst was filtered off using a pad of celite. Most of the EtOH was removed in vacuo and the residue was diluted with 1N HCl aqueous solution. The aqueous phase was extracted with AcOEt then basified to pH 13 and extracted twice with AcOEt. These combined organic layers were dried over MgSO4 and concentrated in vacuo to yield 1-(3-methoxy-phenyl)-1-methyl-ethylamine (F15) (290 mg, 53%) as a yellow gum.

Workup

  1. temperaturecooled to room temperature
  2. filtrationthe catalyst was filtered off
  3. customMost of the EtOH was removed in vacuo
  4. additionthe residue was diluted with 1N HCl aqueous solution
  5. extractionThe aqueous phase was extracted with AcOEt
  6. extractionextracted twice with AcOEt
  7. dry with materialThese combined organic layers were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-656430813be44272a8ac4c1e692987aa
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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