Hydrazine hydrate (1:1) → 14-Aminotetradecan-1-ol

HRID 1740780Notes

Reaction equation

HRID 1740780 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1C(=O)C2=CC=CC=C2C1=O.O.NN>CO>[NH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21833210HCID 21833210, compound

Product 1

HCID 1395603314-Aminotetradecan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of N-(14-hydroxytetradecyl)phthalimide in 100 ml of methanol was added 0.87 g of hydrazine monohydrate and the mixture was heated under reflux for 3 hours. The reaction solution was distilled under reduced pressure and the residue was diluted with a 1N aqueous solution of sodium hydroxide and then extracted twice with chloroform. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then distilled under reduced pressure. Chromatography over silica gel afforded the title compound as a colorless crystal.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. distillationThe reaction solution was distilled under reduced pressure
  4. additionthe residue was diluted with a 1N aqueous solution of sodium hydroxide
  5. extractionextracted twice with chloroform
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-3f195f3ffe874dbabc69248aede8e8f9
Source dataset
uspto-grants-1999_10
Patent number
US05972943

Reaction notes

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