HCID 68552376, compound → 460078-00-6

HRID 1816850Notes

Reaction equation

HRID 1816850 reaction equation
COC1C=CC(C[NH:8][CH2:9][CH2:10][CH:11]([CH2:24][CH2:25][NH:26]CC2C=CC(OC)=CC=2)[CH2:12][CH2:13][NH:14]CC2C=CC(OC)=CC=2)=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:8][CH2:9][CH2:10][CH:11]([CH2:24][CH2:25][NH2:26])[CH2:12][CH2:13][NH2:14]

Participants

4

Reactant 1

HCID 68552376HCID 68552376, compound

Product 1

HCID 9942175460078-00-6Yield 50%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

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 identical with the previously described Example 1.

Workup

  1. custom3 bar, 100° C.
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate was washed with methanol
  4. customThe combined organic phase was evaporated
  5. distillationthe residue was distilled under vacuum (1×10−2, 110° C.)

Sources & evidence

ORD record
ord-5841f21f61df437987ab149fcc5db054
Source dataset
uspto-grants-2009_10
Patent number
US07597875B2

Reaction notes

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