Phenylhydrazine hydrochloride → 1-Acetyl-4-(2,4-dichlorobenzoyl)piperidine phenylhydrazone

HRID 1722168Notes

Reaction equation

HRID 1722168 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl.[C:21]1([NH:27][NH2:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])(=O)C.[Na+]>C(O)(C)C>[C:21]1([NH:27][N:28]=[C:10]([CH:7]2[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]2)[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 60962Phenylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 130763874-(2,4-dichlorobenzoyl)-N-acetylpiperidine

Product 1

HCID 886046701-Acetyl-4-(2,4-dichlorobenzoyl)piperidine phenylhydrazoneYield 49.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred mixture of 1-acetyl-4-(2,4-dichlorobenzoyl)piperidine (33.0 g, 0.11 mol.), phenylhydrazine hydrochloride (34.2 g) and anhydrous sodium acetate in isopropanol was refluxed for 2 hours. The reaction was stirred overnight (about 16 hours) at ambient temperature. The reaction was filtered and the filter cake was washed with ether and then dispersed into water. The water insoluble solid was collected and dried to yield 21.3 g of the product, mp 209°-211° C. Concentration of the filtrate afforded an oil which on standing one week partially solidified. The resultant mixture was triturated with CH3CN and an additional 7.5 g of the product 1-acetyl-4-(2,4-dichlorobenzoyl)piperidine phenylhydrazone was obtained.

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationThe reaction was filtered
  3. washthe filter cake was washed with ether
  4. additiondispersed into water
  5. customThe water insoluble solid was collected
  6. customdried

Sources & evidence

ORD record
ord-fe8dda497c8a4254ac7860782f4eb4d9
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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