Phenylhydrazine hydrochloride → HCID 86741572, compound

HRID 1722147Notes

Reaction equation

HRID 1722147 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1)=O.Cl.[C:18]1([NH:24][NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(=O)C.[Na+]>C(O)CCC>[C:18]1([NH:24][N:25]=[C:4]([CH:6]2[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)[C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[F:1])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 60962Phenylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 131803174-(2-Fluorobenzoyl)-1-methylpiperidine

Product 1

HCID 86741572HCID 86741572, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 14.6 g of 4-(2-fluorobenzoyl)-1-methylpiperidine, 12.0 g of phenylhydrazine hydrochloride and 16.0 g of sodium acetate in 280 ml of n-butanol was heated under reflux for 3.5 hrs. The reaction mixture was cooled, filtered and concentrated. The residue was washed with ether to yield 17 g (83%) of 4-(2-fluorobenzoyl)-1-methylpiperidine phenylhydrazone, mp 131°-134° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3.5 hrs
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe residue was washed with ether

Sources & evidence

ORD record
ord-880850b341c444d085ed9e0fe8da0b9c
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

Loading…