Potassium Carbonate → 2-(4-Octylphenylamino)acetonitrile

HRID 2046031Notes

Reaction equation

HRID 2046031 reaction equation
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br[CH2:17][C:18]#[N:19].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([NH:13][CH2:17][C:18]#[N:19])=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 853464-Octylaniline

Product 1

HCID 866606032-(4-Octylphenylamino)acetonitrileYield 472.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-n-octylaniline (0.21 g; 1 mmol), BrCH2CN (0.156 mmol; 1.3 mmol) and K2CO3 (0.28 g; 2 mmol) in anhydrous CH3CN (3 ml) was stirred overnight at ˜60° C. under N2, then concentrated under reduced pressure. The residue was partitioned between CH2Cl2 (20 ml) and H2O (10 ml). The organic phase was dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by crystallization from hexane to give the title compound (0.18 g; 74%) as creamy solid. 1H-NMR (CDCl3) 7.06 (d, 2H, J=8.48 Hz); 6.63 (d, 2H, J=8.48 Hz); 4.06 (d, 2H, J=5.75 Hz); 3.83 (broad m, 1H); 2.51 (t, 2H, J=7.92 Hz); 1.55 (m, 3H); 1.27 (m, 10H); 0.86 (t, 3H, J=6.87 Hz).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 (20 ml) and H2O (10 ml)
  3. dry with materialThe organic phase was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customthe residue was purified by crystallization from hexane

Sources & evidence

ORD record
ord-743533e850ba466aab5ce1c4ce566a93
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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