Hydrazine hydrate (1:1) → 1-Amino-11-azido-3,6,9-trioxaundecane

HRID 1714710Notes

Reaction equation

HRID 1714710 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]1C(=O)C2=CC=CC=C2C1=O)=[N+:2]=[N-:3].O.NN>CO>[NH2:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14827674HCID 14827674, compound

Product 1

HCID 27352801-Amino-11-azido-3,6,9-trioxaundecaneYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Azido-11-phtalimido-3,6,9-trioxaundecane (8, Example 3, 2.0 g, 5.74 mmol), is treated with 1.0 ml 55% hydrazine hydrate in 50 ml abs. methanol and heated to reflux for 2 h. After cooling to room temperature, the mixture is concentrated in vacuo, diluted with 50 ml of water and treated with 5 ml conc. HCl. All precipitate is filtered off, the aqueous filtrate neutralized with NaOH, and the solvent removed in vacuo. The residue is dissolved in dichloromethane, and washed with 3 N NaOH and water. The organic phase is dried over MgSO4 and concentrated in vacuo yielding 0.63 g (2.9 mmol, 51%) of a colourless oil, which is used in the next step without further purification.

Workup

  1. temperatureto reflux for 2 h
  2. concentrationthe mixture is concentrated in vacuo
  3. additiondiluted with 50 ml of water
  4. additiontreated with 5 ml conc. HCl
  5. filtrationAll precipitate is filtered off
  6. customthe solvent removed in vacuo
  7. dissolutionThe residue is dissolved in dichloromethane
  8. washwashed with 3 N NaOH and water
  9. dry with materialThe organic phase is dried over MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25ce740fe363454f89633ac405601f75
Source dataset
uspto-grants-2010_09
Patent number
US07799524B2

Reaction notes

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