Piperidine → Farampator

HRID 1872660Notes

Reaction equation

HRID 1872660 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:2]=12.[C:13]([C:20]1[NH:21][CH:22]=[CH:23]N=1)([C:15]1NC=CN=1)=O.N1CCCCC1>ClCCl>[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]([N:21]3[CH2:20][CH2:13][CH2:15][CH2:23][CH2:22]3)=[O:12])[CH:8]=[CH:9][C:2]=12

Participants

5

Reactant 3

HCID 8082PiperidineHCID 27354542,1,3-Benzoxadiazole-5-carboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 4118151Farampator

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzofurazan-5-carboxylic acid (2.0 g, 12.2 mmol) was suspended in 10 mL dichloromethane. Carbonyl diimidazole (2.0 g, 12.3 mmol) was added, which caused dissolution with gas evolution. The resulting yellow solution was stirred for 40 minutes at room temperature, following which, piperidine (1.2 g, 14.1 mmol) was added. The solution was stirred overnight and then concentrated onto silica. Product was eluted with hexane/ethyl acetate (2:1) and purified by distillation in a kugelrohr at 155-170° C. and 0.5 mmHg. 1-(Benzofurazan-5-ylcarbonyl)piperidine, 2 (2.78 g, 99%), initially a pale yellow oil, crystallized upon cooling. M.p. 88.5-90.5° C. IR: 2938, 2857, 1630, 1519, 1439, 1266, 1223, 996, 881, 816, and 740 cm-1. 1H NMR (500 MHz): δ 7.90 (1H, d, J=9.7 Hz); 7.84 (1H, s); 7.44 (1H, dd, J=9.4 and 1.4 Hz); 3.74 (2H, br s); 3.39 (2H, br s); 1.72 (4H, br s); and 1.57 ppm (2H, br s).

Workup

  1. dissolutiondissolution with gas evolution
  2. additionwas added
  3. stirringThe solution was stirred overnight
  4. concentrationconcentrated onto silica
  5. washProduct was eluted with hexane/ethyl acetate (2:1)
  6. distillationpurified by distillation in a kugelrohr at 155-170° C.
  7. custom1-(Benzofurazan-5-ylcarbonyl)piperidine, 2 (2.78 g, 99%), initially a pale yellow oil, crystallized
  8. temperatureupon cooling

Sources & evidence

ORD record
ord-84b5bb45f32a458b87faf35b9b4359e8
Source dataset
uspto-grants-2000_08
Patent number
US06110935

Reaction notes

Loading…