Phenylhydrazine hydrochloride → HCID 86741574, compound

HRID 845658Notes

Reaction equation

HRID 845658 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]([Br:17])=[CH:13][C:12]=2[F: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]([Br:17])=[CH:13][C:12]=2[F:18])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 60962Phenylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 14032496HCID 14032496, compound

Product 1

HCID 86741574HCID 86741574, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-acetyl-4-(4-bromo-2-fluorobenzoyl)piperidine (16.6 g, 0.051 mol), phenylhydrazine hydrochloride (16.6 g, 0.11 mol), sodium acetate, (22.2 g) and isopropanol (250 ml) was stirred and refluxed for 4 hours. The reaction stood at ambient temperature for 16 hours, and then was filtered. The filtercake was treated with water, and the insoluble hydrazone was collected and dried to yield 13.7 g. The isopropanol filtrate was concentrated in vacuo to a solid, which when triturated with ether yielded 6.1 g more of the hydrazone (total yield 19.8 g; 93%). The phenylhydrazone was a mixture of the two geometric isomers. A 3.5 g sample of the compound was recrystallized from isopropanol to yield 2.1 g of the phenylhydrazone; m.p. 174°-176° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. filtrationwas filtered
  3. additionThe filtercake was treated with water
  4. customthe insoluble hydrazone was collected
  5. customdried
  6. customto yield 13.7 g
  7. concentrationThe isopropanol filtrate was concentrated in vacuo to a solid, which when
  8. customtriturated with ether

Sources & evidence

ORD record
ord-707932c552a346138a1b610e0e89de71
Source dataset
uspto-grants-1988_07
Patent number
US04758668

Reaction notes

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