Sodium Hydroxide → N~1~-(3-Aminopropyl)-N~1~-benzylpropane-1,3-diamine

HRID 1251307Notes

Reaction equation

HRID 1251307 reaction equation
[CH2:1]([N:8]([CH2:13][CH2:14][C:15]#[N:16])[CH2:9][CH2:10][C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>[Ni].C(O)C>[CH2:1]([N:8]([CH2:9][CH2:10][CH2:11][NH2:12])[CH2:13][CH2:14][CH2:15][NH2:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11171892N-Benzylbis(2-cyanoethyl)amine

Product 1

HCID 12403256N~1~-(3-Aminopropyl)-N~1~-benzylpropane-1,3-diamineYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 43.3 g (0.203 mol) of N-benzylbis(2-cyanoethyl)amine, 7.8 g of a 50% aqueous slurry of Raney nickel and 90 mL of a 1.4 M solution of NaOH in 95% ethanol was hydrogenated in a Parr apparatus for 48 h. The catalyst was removed by filtration and washed with 80 mL of 95% ethanol. The combined filtrates were concentrated by rotary evaporation. A solution of the residue in 100 mL of hexane/chloroform (1:1, v/v) was dried over Na2SO4, filtered and concentrated by rotary evaporation. Removal of solvent residues under vacuum (0.5 mm) afforded 40.3 g (90%) of product as a yellow oil. 1H NMR (CDCl3/TMS) δ7.31 (m, 5 H), 3.52 (s, 2 H), 2.70 (t, J=6.8 Hz, 4 H), 2.45 (t, J=6.8 Hz, 4 H), 1.60 (quint., J=6.8 Hz, 4 H), 1.26 (s, 4 H). 13C NMR (CDCl3) δ139.5, 128.3, 127.7, 126.3, 58.3, 50.9, 40.0, 30.6. IR (film, cm−1) 3360 (br), 3270 (br), 3070 (w), 3050 (w), 3020 (m), 2920 (br. s), 2850 (s), 2800 (s), 1600 (s), 1485 (s), 1450 (s), 1360 (m), 1110 (br), 1070 (m), 1020 (m) 730 (m), 690 (m).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with 80 mL of 95% ethanol
  3. concentrationThe combined filtrates were concentrated by rotary evaporation
  4. dry with materialA solution of the residue in 100 mL of hexane/chloroform (1:1, v/v) was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customRemoval of solvent residues under vacuum (0.5 mm)

Sources & evidence

ORD record
ord-222fcefe43e0440aa0435c9d3570c449
Source dataset
uspto-grants-2002_01
Patent number
US06342492B1

Reaction notes

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