Hydrazine hydrate (1:1) → 1,1,1-Tris(aminoethoxymethyl)ethane

HRID 36830Notes

Reaction equation

HRID 36830 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][O:8][CH2:9][C:10]([CH2:27][O:28][CH2:29][CH2:30][N:31]2C(=O)C3=CC=CC=C3C2=O)([CH2:12][O:13][CH2:14][CH2:15][N:16]2C(=O)C3=CC=CC=C3C2=O)[CH3:11])C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:31][CH2:30][CH2:29][O:28][CH2:27][C:10]([CH2:9][O:8][CH2:7][CH2:6][NH2:5])([CH2:12][O:13][CH2:14][CH2:15][NH2:16])[CH3:11]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 540827261,1,1-Tris(phthalimidoethoxymethyl)ethane

Product 1

HCID 542459851,1,1-Tris(aminoethoxymethyl)ethaneYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1,1,1-tris(phthalimidoethoxymethyl)ethane (4.0 g, 6.30 mmol) in 100 mL of absolute ethanol was heated to 50C. Then a 55% solution of hydrazine hydrate (3.7 mL, 63.00 mmol) was added dropwise and the resulting mixture was heated at 50° C. for 5 hrs. The reaction was cooled to 25° C. and the solids were filtered. The filtrate was evaporated to give an oil which was purified over reversed phase packing (C-18) using a methanol/water gradient as eluant to yield 1,1,1-tris(aminoethoxymethyl)ethane (1.3 g, 5.22 mmol, 83 % ).

Workup

  1. temperatureThe reaction was cooled to 25° C.
  2. filtrationthe solids were filtered
  3. customThe filtrate was evaporated
  4. customto give an oil which
  5. customwas purified over reversed phase packing (C-18)

Sources & evidence

ORD record
ord-f8a55913bfc74bafbad7ea2f32f634cf
Source dataset
uspto-grants-1995_05
Patent number
US05417959

Reaction notes

Loading…