Hydrazine hydrate (1:1) → 6-(2-Methyl-1,3-dioxolan-2-yl)hexan-1-amine

HRID 1164496Notes

Reaction equation

HRID 1164496 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2C(=O)C3=CC=CC=C3C2=O)[O:6][CH2:5][CH2:4][O:3]1.O.NN>C(O)C>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[O:3][CH2:4][CH2:5][O:6]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20511312N-[6-(2-Methyl-1,3-dioxolan-2-yl)hexyl]phthalimide

Product 1

HCID 130938726-(2-Methyl-1,3-dioxolan-2-yl)hexan-1-amineYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 125.25 g (0.395 mole) of N-[6-(2-methyl-1,3-dioxolan-2-yl)hexyl]phthalimide, 23 ml of 85% hydrazine hydrate, and 370 ml of 95% ethanol was refluxed for four hours, cooled, filtered and stripped. The residue was mixed with 500 ml of water, basified with 2 N NaOH solution and extracted with methylene chloride. The organic layer was separated, dried over anhydrous potassium carbonate, filtered, and stripped to an orange oil. This material was distilled to give 35.70 g (64%) of clear oil bp 80°-83° (0.100 mm).

Workup

  1. temperaturewas refluxed for four hours
  2. temperaturecooled
  3. filtrationfiltered
  4. additionThe residue was mixed with 500 ml of water
  5. extractionextracted with methylene chloride
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous potassium carbonate
  8. filtrationfiltered
  9. distillationThis material was distilled

Sources & evidence

ORD record
ord-82eb6438fb3043a6a2c519dfd2fb909c
Source dataset
uspto-grants-1983_01
Patent number
US04370335

Reaction notes

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