Hydrazine hydrate (1:1) → HCID 23004174, compound

HRID 1978339Notes

Reaction equation

HRID 1978339 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16]C3C=CC=C4C(NC(=O)C=34)=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:29]N>C(O)C>[NH2:29][CH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21993914HCID 21993914, compound

Product 1

HCID 23004174HCID 23004174, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 10.38 g (28.64 mM) of 4-(4-phenylpiperidin-1-yl)butan-1-ylphthalimide in ethanol (160 ml) was added 4.2 ml (86.58 mM) of hydrazine monohydrate at room temperature and the mixture was refluxed for 1.5 hours. The white solid that formed was filtered off and the solvent was distilled off under reduced pressure. The residue was diluted with aqueous solution of sodium hydroxide and extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide the title compound.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. customThe white solid that formed
  3. filtrationwas filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe residue was diluted with aqueous solution of sodium hydroxide
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over MgSO4
  9. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-d8a62aa0af6a4191831b49b4bff24086
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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