Water → 2-(4-Methoxyphenyl)-2-methylpropan-1-amine

HRID 242063Notes

Reaction equation

HRID 242063 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])=[CH:11][CH:10]=1.[OH-].[Na+].O>C(OCC)C>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:19])([CH3:18])[CH2:16][NH2:17])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2191662-(4-Methoxyphenyl)-2-methylpropanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 35813642-(4-Methoxyphenyl)-2-methylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

A reaction vessel was charged with lithiumaluminium hydride (0.433 g, 11.41 mmol) and dry diethyl ether (20 mL). After cooling to 5° C. a solution of 2-(4-methoxyphenyl)-2-methylpropanenitrile (2.00 g, 11.41 mmol) in dry diethylether (10 mL) was added dropwise. The reaction mixture was stirred at 5° C. for 2 h. The reaction mixture was then cooled in an ice bath and 2N aqueous sodium hydroxide solution (0.8 mL) and water (1.5 mL) were added. After stirring for 20 min additional water (40 mL) was added and the reaction mixture was extracted with ethyl acetate (2×30 mL). The combined extracts were dried (MgSO4) and the solvent was evaporated in vacuo. The crude product (1.94 g, 10.82 mmol) was used without further purification for the next step.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was then cooled in an ice bath
  3. additionwas added
  4. extractionthe reaction mixture was extracted with ethyl acetate (2×30 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-136d45100f5e456f8a709651efd03beb
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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