Hydrazine hydrate (1:1) → 12-Amino-1-dodecanol

HRID 1003308Notes

Reaction equation

HRID 1003308 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][N:14]1C(=O)C2=CC=CC=C2C1=O.O.NN>CO>[NH2:14][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 18796407N-(12-hydroxydodecyl)phthalimide

Product 1

HCID 518202012-Amino-1-dodecanolYield 74.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 600 ml of methanol was dissolved while warming 48.0 g of N-(12-hydroxydodecyl)phthalimide, 50 ml of hydrazine monohydrate was added at room temperature with stirring and the mixture was stirred overnight. The crystal thus separated out was filtered off and the solvent was distilled off. The residue was extracted with hot chloroform and insolubles were filtered off. The filtrate was distilled, the residue was extracted with hot chloroform (100 ml×3) and then the solvent was distilled off. The residue was dissolved in methanol and recrystallization from methanol-ethyl acetate gave 21.6 g of the title compound as a crystal.

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred overnight
  3. customThe crystal thus separated out
  4. filtrationwas filtered off
  5. distillationthe solvent was distilled off
  6. extractionThe residue was extracted with hot chloroform and insolubles
  7. filtrationwere filtered off
  8. distillationThe filtrate was distilled
  9. extractionthe residue was extracted with hot chloroform (100 ml×3)
  10. distillationthe solvent was distilled off
  11. dissolutionThe residue was dissolved in methanol
  12. customrecrystallization from methanol-ethyl acetate

Sources & evidence

ORD record
ord-c7baf5ca20614e9b99493d1848dede8b
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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