Hydrazine hydrate (1:1) → HCID 18933282, compound

HRID 1598382Notes

Reaction equation

HRID 1598382 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:10][CH2:11][N:12]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:13][CH2:14][N:15]2C(=O)C3=CC=CC=C3C2=O)=[CH:4][CH:3]=1.O.NN>CO>[NH2:15][CH2:14][CH2:13][N:12]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:11][CH2:10][N:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:33](=[O:34])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18933363HCID 18933363, compound

Product 1

HCID 18933282HCID 18933282, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[7-(p-fluorophenyl)-3,6-di(tert-butoxycarbonyl)-3,6-diaza-1-heptyl]phthalimide (14.5 g, 26.7 mmol) in methanol (200 ml) was added hydrazine monohydrate (1.4 ml) and heated under reflux for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue was added chloroform (200 ml) and washed with aqueous ammonia (150 ml×2). The organic layer was dried over anhydrous potassium carbonate and the solvent was distilled off under reduced pressure. The resulting colorless oily substance was chromatographed using silica gel column to give 4.7 g of the title compound from the fraction from methylene chloride-methanol-aqueous ammonia (90/10/0.5) as a colorless oily substance. Yield=43%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the residue was added chloroform (200 ml)
  6. washwashed with aqueous ammonia (150 ml×2)
  7. dry with materialThe organic layer was dried over anhydrous potassium carbonate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting colorless oily substance was chromatographed

Sources & evidence

ORD record
ord-15286742ea4a4228a433bc62bb0749f7
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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