Hydrazine → 4-Cyano-4-phenylpiperidine propylamine

HRID 278920

Reaction equation

HRID 278920 reaction equation
[C:1]([C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11]C2C=CC=C3C(NC(=O)C=23)=O)[CH2:5][CH2:4]1)#[N:2].[NH2:29]N>CO>[C:1]([C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][NH2:29])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 227252233-(4-Cyano-4-phenylpiperidin-1-yl)propylphthalimide

Product 1

HCID 98377104-Cyano-4-phenylpiperidine propylamineYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(4-cyano-4-phenylpiperidin-1-yl)propylphthalimide (112 g, 0.3 mol) in methanol (1.5 L), hydrazine (30 mL) was added and the mixture was stirred and refluxed for 20 hours. It was cooled, the white solid formed was filtered and washed with more methanol (200 mL). Solvent was evaporated from the filtrate and residue was dried under vacuum for 4 hours. Chloroform (500 mL) was added to this, stirred for 1 hour and filtered. The white solid was washed with more chloroform (200 mL), the solvent was evaporated from the combined filtrates to leave the product as an oil (70 g, 96%).

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureIt was cooled
  3. customthe white solid formed
  4. filtrationwas filtered
  5. washwashed with more methanol (200 mL)
  6. customSolvent was evaporated from the filtrate and residue
  7. customwas dried under vacuum for 4 hours
  8. additionChloroform (500 mL) was added to this,
  9. stirringstirred for 1 hour
  10. filtrationfiltered
  11. washThe white solid was washed with more chloroform (200 mL)
  12. customthe solvent was evaporated from the combined filtrates

Sources & evidence

ORD record
ord-cd33099329444c3fb641cf95353f784b
Source dataset
uspto-grants-2002_03
Patent number
US06362182B1

Linked notes

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