Hydrazine → 4-Cyano-4-phenylpiperidine propylamine

HRID 1275226Notes

Reaction equation

HRID 1275226 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 h. 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 h. Chloroform (500 mL) was added to this, stirred for 1 h 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 h
  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 h
  8. additionChloroform (500 mL) was added to this,
  9. stirringstirred for 1 h
  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-8672b2d1be3f445697149fcdeee09e06
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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