Phenylhydrazine hydrochloride → HCID 86741574, compound

HRID 2107440Notes

Reaction equation

HRID 2107440 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; mp 174°-176° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. filtrationwas filtered The filtercake
  3. additionwas 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-eed1264cdd674f56bf1c0c734f34416b
Source dataset
uspto-grants-1990_06
Patent number
US04933460

Reaction notes

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