Sodium hydride → HCID 20517738, compound

HRID 2198873Notes

Reaction equation

HRID 2198873 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([CH:17]=1)[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)=[O:8].[H-].[Na+].F[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([CH:17]=1)[C:7]([N:9]([CH:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29])=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 20517713HCID 20517713, compound

Product 1

HCID 20517738HCID 20517738, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 31.3 g 5-chloro-2-fluoro-N-(1-methyl-4-piperidinyl)-benzamide, 5.6 g of 55% sodium hydride/oil dispersion and 250 ml dimethylformamide are stirred at 45° for 40 minutes. Thereafter 29.7 g 2-fluoro-nitrobenzene are added and stirring is continued at 50° for 80 hours. The solvent is evaporated in vacuo and the residue partitioned between 2 N hydrochloric acid and toluene. The acid phase is made alkaline with 2 N sodium hydroxide and extracted with methylene chloride. The organic phase is dried and evaporated in vacuo to give the heading compound, which recrystallised from ether has a m.p. 164°-166°.

Workup

  1. stirringstirring
  2. waitis continued at 50° for 80 hours
  3. customThe solvent is evaporated in vacuo
  4. customthe residue partitioned between 2 N hydrochloric acid and toluene
  5. extractionextracted with methylene chloride
  6. customThe organic phase is dried
  7. customevaporated in vacuo
  8. customto give the heading compound, which
  9. customrecrystallised from ether

Sources & evidence

ORD record
ord-457e7fdddc2248a4a320457122ef7985
Source dataset
uspto-grants-1982_11
Patent number
US04360525

Reaction notes

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