Reaction #1960667

Reaction equation

1,1,1-tris[2-(p-methoxybenzylamino)ethyl]methane

→

1,1,1-tris(2-aminoethyl)methane

Yield 50.0%

Solvents

methanol

Conditions

Workup

1. 1
   Other3 bar, 100° C.
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Washthe filtrate was washed with methanol
4. 4
   OtherThe combined organic phase was evaporated
5. 5
   workup.DISTILLATIONthe residue was distilled under vacuum (1×10−2, 110° C.)

Procedure

1,1,1-tris[2-(p-methoxybenzylamino)ethyl]methane (20.0 gram, 0.036 mol) was dissolved in methanol (100 ml) and Pd(OH)2 (5.0 gram) was added. The mixture was hydrogenated (3 bar, 100° C., in an autoclave) and stirred for 5 hours. Pd(OH)2 was added in two more portions (2×5 gram) after 10 and 15 hours respectively. The reaction mixture was filtered and the filtrate was washed with methanol. The combined organic phase was evaporated and the residue was distilled under vacuum (1×10−2, 110° C.) to give 2.60 gram (50%) of 1,1,1-tris(2-aminoethyl)methane.

Source