4-(1-Cyano-1-methylethyl)benzonitrile → 2-[4-(Aminomethyl)phenyl]-2-methylpropanenitrile

HRID 419972Notes

Reaction equation

HRID 419972 reaction equation
[C:1]([C:3]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)([CH3:5])[CH3:4])#[N:2].COCCO[AlH2-]OCCOC.[Na+]>C1COCC1>[NH2:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([C:3]([CH3:5])([CH3:4])[C:1]#[N:2])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 101763144-(1-Cyano-1-methylethyl)benzonitrileHCID 16684438Red-Al

Product 1

HCID 582984752-[4-(Aminomethyl)phenyl]-2-methylpropanenitrileYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(1-cyano-1-methylethyl)benzonitrile (2.28 g, 13.41 mmol) is dissolved in dry THF and the solution cooled to 0° C. Red-Al (85% soln in toluene, 2.62 ml, 13.41 mmol of hydride) is added and the reaction stirred at 0° C. for 4 hours. The mixture is quenched with methanol and concentrated under vacuo. The residue is dissolved in CH2Cl2, washed with 2 portions of water, dried over magnesium sulfate, filtered and evaporated to dryness. The crude is purified by normal phase MPLC (SiO2, DCM to DCM/MeOH 3:1), giving 2-[4-(aminomethyl)phenyl]-2-methylpropanenitrile (900 mg, 5.17 mmol, 39%) as a colorless oil. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.68 (s, 6H) 4.00-4.05 (m, 2H) 7.55 (q, J=8.59 Hz, 4H) 8.35 (broad s, 2H).

Workup

  1. customThe mixture is quenched with methanol
  2. concentrationconcentrated under vacuo
  3. dissolutionThe residue is dissolved in CH2Cl2
  4. washwashed with 2 portions of water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude is purified by normal phase MPLC (SiO2, DCM to DCM/MeOH 3:1)

Sources & evidence

ORD record
ord-35afda4f0bb24ccba63c39cc55b5c9ce
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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