4-Fluorophenylhydrazine hydrochloride → HCID 86741573, compound

HRID 845642Notes

Reaction equation

HRID 845642 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.[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][NH2:26])=[CH:21][CH:20]=1.C([O-])(=O)C.[Na+]>C(O)CCC>[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][N:26]=[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:21][CH:20]=1

Participants

5

Reactant 3

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 131803174-(2-Fluorobenzoyl)-1-methylpiperidine

Product 1

HCID 86741573HCID 86741573, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A stirred mixture of 21.8 g of 4-(2-fluorobenzoyl)-1-methylpiperidine, 20.25 g of 4-fluorophenyl hydrazine hydrochloride and 25.0 g of sodium acetate in 420 ml of n-butanol was heated under reflux for 8 hrs. The mixture was cooled, filtered, and concentrated. The residue was washed with ether to give 7.5 g (23%) of 4-(2-fluorobenzoyl)-1-methylpiperidine 4-fluorophenylhydrazone, hydrazone, mp 125°-126° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hrs
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe residue was washed with ether

Sources & evidence

ORD record
ord-86d414aad31640599e333420fd70998a
Source dataset
uspto-grants-1988_07
Patent number
US04758668

Reaction notes

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