Piperidine → Farampator

HRID 427274Notes

Reaction equation

HRID 427274 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 4118151FarampatorYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzofurazan-5-carboxylic acid (1 g, 5.6 mmol) was suspended with stirring in 15 mL dichloromethane to which was added carbonyl diimidazole (0.90 g, 5.6 mmol). Gas evolved and the resulting solution was stirred for 40 minutes at which time piperidine (0.5 g, 5.9 mmol) was added with stirring. The reaction solution was concentrated onto silica and product was eluted with hexanelethyl acetate (3:1). Recrystallization from 2-propanol/hexane (1:10) yielded 1-(benzofurazan-5-ylcarbonyl)piperidine (0.94 g, 69%) as a yellow solid with, m.p. 94.5-96.5° C. IR: 2938, 2855, 1620, 1612, 1528, 1487, 1435, 1257, 1233, 1018, 1000, 852, 811, and 747 cm−1. 1H NMR (500 MHz): δ 7.10-7.80 (3H, br s); 3.72 (2H br s); 3.39 (2H, br s); 1.72 (4H, br s); and 1.54 ppm (2H, br s).

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated onto silica and product
  3. washwas eluted with hexanelethyl acetate (3:1)
  4. customRecrystallization from 2-propanol/hexane (1:10)

Sources & evidence

ORD record
ord-f4b3efe1eda84b1e86ea8175abe48e78
Source dataset
uspto-grants-2001_11
Patent number
US06313115B1

Reaction notes

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