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

HRID 1251306Notes

Reaction equation

HRID 1251306 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 CH2CO2 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) δ137.5, 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 CH2CO2 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-f3d29ba147ad44e99b1f6ee1d085ea4b
Source dataset
uspto-grants-2002_01
Patent number
US06342492B1

Reaction notes

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