Sodium Iodide → HCID 215909, compound

HRID 437225Notes

Reaction equation

HRID 437225 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:17]1([F:28])[CH:22]=[CH:21][C:20]([C:23](=[O:27])[CH2:24][CH2:25][CH3:26])=[CH:19][CH2:18]1.[I-].[Na+]>CN(C)C=O>[F:28][C:17]1[CH:18]=[CH:19][C:20]([C:23](=[O:27])[CH2:24][CH2:25][CH2:26][N:13]2[CH2:14][CH2:15][CH:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][CH2:12]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 118120N-4-PiperidylbenzamideHCID 86734191HCID 86734191, compound

Product 1

HCID 215909HCID 215909, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Benzamidopiperidine (2.0 g.), 4'-chloro-p-fluorobutyrophenone (1.0 g.) and a trace of sodium iodide in dimethylformamide (5 ml.) were maintained at 70° C. for 18 hours. On cooling, the solid which separated was collected, suspended in water, and refiltered. Recrystallisation from ethanol-water gave the title compound (0.52 g.), m.p. 161°-2° C. (Found: C, 71.9; H, 6.85; N, 7.5. C22H25FN2O2 requires C, 71.7; H, 6.8; N, 7.6%).

Workup

  1. temperatureOn cooling
  2. customthe solid which separated
  3. customwas collected
  4. customRecrystallisation from ethanol-water

Sources & evidence

ORD record
ord-d8c6bc5389654ddcadccd42c15feda44
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Reaction notes

Loading…