N-(2-Aminoethyl)piperidine → HCID 18987437, compound

HRID 2396495Notes

Reaction equation

HRID 2396495 reaction equation
ClC(Cl)(Cl)[C:3]1[O:7][N:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:17])[CH:9]=2)[N:4]=1.[NH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>>[NH2:20][CH:21]([C:3]1[O:7][N:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:17])[CH:9]=2)[N:4]=1)[CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 18987424HCID 18987424, compound

Product 1

HCID 18987437HCID 18987437, compound

Conditions

Temperature
120 °C

Procedure

5-Trichloromethyl-3-[1-methyl-1H-indol-3-yl]-1,2,4-oxadiazole (0.100 g, 0.316 mmol) (D8) was dissolved with stirring in 1-(2-aminoethyl) piperidine (0.8 ml) and heated to 120° C. After 0.5 h, the reaction mixture was allowed to cool and was partitioned between EtOAc and water. The organic layer was then washed with water (1×), dried (Na2SO4) and evaporated under reduced pressure to give a yellow oil which was purified by silica gel chromatography (10% MeOH in EtOAc as eluant) to give the title compound as a colourless oil that crystallised on standing (0.095 g, 93%).

Workup

  1. temperatureto cool
  2. customwas partitioned between EtOAc and water
  3. washThe organic layer was then washed with water (1×)
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customto give a yellow oil which
  7. customwas purified by silica gel chromatography (10% MeOH in EtOAc as eluant)

Sources & evidence

ORD record
ord-dc6c0ada4cc34ef9b2e4027dede478f0
Source dataset
uspto-grants-1996_02
Patent number
US05492919

Reaction notes

Loading…