Hydrazine hydrate (1:1) → Ammonia

HRID 414617Notes

Reaction equation

HRID 414617 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]2C(=O)C3=CC=CC=C3C2=O)=[CH:3][CH:2]=1.O.NN>C(O)C>[NH3:14].[C:1]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:2]=[CH:3][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21281403HCID 21281403, compound

Product 2

HCID 222AmmoniaHCID 13957284HCID 13957284, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[6-(4-biphenyloxy)hexyl]phthalimide (17 g), ethanol (500 ml) and hydrazine hydrate (10 ml) was heated at reflux for 16 hours, cooled to room temperature, filtered, and evaporated to dryness. The remaining material was stirred with dichloromethane (500 ml), filtered and evaporated to dryness. The crude product was chromatographed on silica gel, eluting with 95:5 dichloromethane:methanolic ammonia, yielding 6-(4-biphenyloxy)-1-aminohexane as an oil, which was converted to the hydrochloride salt, (m.p. 201°-202° C.), according to the method of Example 3.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationfiltered
  4. customevaporated to dryness
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product was chromatographed on silica gel
  8. washeluting with 95:5 dichloromethane

Sources & evidence

ORD record
ord-d449bae39c3b4816baabf9de9396e4d3
Source dataset
uspto-grants-1988_12
Patent number
US04792570

Reaction notes

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