Nitroethane → 2,2-Dimethylpropyl 4-[4-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-2-yl]-1-piperazinecarboxylate

HRID 421829Notes

Reaction equation

HRID 421829 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)[CH:4]=1)#[N:2].[N+:23]([CH2:26][CH3:27])([O-])=[O:24].C1(N=C=O)C=CC=CC=1>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:27][C:26]1[N:2]=[C:1]([C:3]2[CH:8]=[CH:7][N:6]=[C:5]([N:9]3[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:13][CH2:14]3)[CH:4]=2)[O:24][N:23]=1

Participants

6

Reactant 3

HCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 119924192,2-Dimethylpropyl 4-(4-cyanopyridin-2-yl)-1-piperazinecarboxylate

Product 1

HCID 119928072,2-Dimethylpropyl 4-[4-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-2-yl]-1-piperazinecarboxylateYield 31.9%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 1140TolueneSolvent

Procedure

2,2-Dimethylpropyl 4-(4-cyanopyridin-2-yl)piperazine-1-carboxylate (301 mg) obtained in Example 2 was dissolved in toluene (5 mL), and nitroethane (82.6 mg), triethylamine (one drop) and phenyl isocyanate (0.238 mL) were added thereto, stirred at room temperature for 1 hour, and then heated under reflux for 2 hours. The reaction liquid was filtered, the filtrate was evaporated, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1) to obtain 114 mg of the entitled compound as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. customThe reaction liquid
  4. filtrationwas filtered
  5. customthe filtrate was evaporated
  6. customthe resulting residue was isolated
  7. custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-17f698e71b6b4f70aa5b793df8651c1a
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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