Water → 2-Methyl-2-phenylpropan-1-amine

HRID 277890Notes

Reaction equation

HRID 277890 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[C:9]#[N:10].O.[OH-].[Na+]>C(OCC)C>[CH3:11][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:7])[CH2:9][NH2:10]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27975912-Methyl-2-phenylpropanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 2106022-Methyl-2-phenylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of lithium aluminium hydride (4.85 g, 0.128 mol) in anhydrous diethyl ether (245 ml) at ambient temperature under argon was added a solution of α,α-dimethylphenylacetonitrile (12.4 g, 0.085 mol) in anhydrous diethyl ether (105 ml) dropwise over 0.5 hour. The resultant was heated at reflux for 3 hours, cooled to ambient temperature and treated with water (4.6 ml), 15% aqueous sodium hydroxide (4.6 ml) and water (13.8 ml) dropwise sequentially. The mixture was stirred for 1.5 hours, filtered and the filtrate dried (Na2SO4) and treated with 1N hydrogen chloride in ether (100 ml). The precipitated solid was filtered and dried to afford the title compound as the hydrochloride salt (9.4 g, 52%).

Workup

  1. temperatureThe resultant was heated
  2. temperatureat reflux for 3 hours
  3. filtrationfiltered
  4. dry with materialthe filtrate dried (Na2SO4)
  5. additiontreated with 1N hydrogen chloride in ether (100 ml)
  6. filtrationThe precipitated solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-5f9a22167e3c4f08bf9905d0420e8268
Source dataset
uspto-grants-2002_03
Patent number
US06358974B1

Reaction notes

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