Benzyl Chloride → N-Benzylbis(2-cyanoethyl)amine

HRID 1376395Notes

Reaction equation

HRID 1376395 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][C:8]#[N:9])#[N:2].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[Na+].C(#N)C>[CH2:10]([N:5]([CH2:6][CH2:7][C:8]#[N:9])[CH2:4][CH2:3][C:1]#[N:2])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 81493,3'-IminodipropionitrileHCID 10340Sodium Carbonate

Product 1

HCID 11171892N-Benzylbis(2-cyanoethyl)amineYield 89%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 50.0 g (0.406 mol) of bis(2-cyanoethyl)amine, 51.45 g (0.406 mol) of benzyl chloride, 1.0 g (6.7 mmol) of sodium iodide, 22.05 g (0.208 mol) of sodium carbonate and 150 mL of acetonitrile was stirred mechanically and heated at reflux under nitrogen for 5 h. The cooled reaction mixture was filtered and the solids were washed with acetonitrile (3×50 mL). The combined filtrates were concentrated by rotary evaporation. A solution of the residue in 100 mL of CH2Cl2 was washed with saturated aqueous Na2S2O3 (2×20 mL) and saturated aqueous NaCl (2×50 mL). The combined aqueous layers were extracted with CH2Cl2 (3×30 mL). The combined CH2Cl2 solutions were dried over MgSO4, filtered and concentrated by rotary evaporation. The residual solvent was removed under vacuum (0.5 mm), yielding 70.4 g (89%) of product as a light yellow oil. 1H NMR (CDCl3 /TMS) δ 7.34 (m, 5 H), 3.70 (s, 2 H), 2.88 (t, J=6.8 Hz, 4 H), 2.44 (t, J=6.8 Hz, 4 H). 13C NMR (CDCl3) δ 137.5, 128.3, 127.4, 118.4, 57.7, 49.1, 16.4. IR (film, cm- 1) 3070 (w), 3050 (m), 3020 (s), 2930 (s), 2830 (s), 2240 (s), 1595 (m), 1575 (w), 1485 (s), 1445 (s), 1415 (s), 1360 (br), 1250 (br), 1125 (s), 1070 (s), 1020 (s), 960 (s), 730 (s), 690 (s).

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 5 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. washthe solids were washed with acetonitrile (3×50 mL)
  6. concentrationThe combined filtrates were concentrated by rotary evaporation
  7. washA solution of the residue in 100 mL of CH2Cl2 was washed with saturated aqueous Na2S2O3 (2×20 mL) and saturated aqueous NaCl (2×50 mL)
  8. extractionThe combined aqueous layers were extracted with CH2Cl2 (3×30 mL)
  9. dry with materialThe combined CH2Cl2 solutions were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated by rotary evaporation
  12. customThe residual solvent was removed under vacuum (0.5 mm)

Sources & evidence

ORD record
ord-09ffbdb771db40e685844500c0163709
Source dataset
uspto-grants-1997_09
Patent number
US05663161

Reaction notes

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