Azidobenzene → HCID 58945818, compound

HRID 2267130Notes

Reaction equation

HRID 2267130 reaction equation
[C:1]1([N:7]=[N+:8]=[N-:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([C:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH:18]=1)#[C:11][CH3:12]>C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:11]([CH3:12])=[C:10]([C:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=3)[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 69319AzidobenzeneHCID 68431041HCID 68431041, compound

Product 1

HCID 58945818HCID 58945818, compoundYield 3.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

The above-prepared phenyl azide (214 mg) and 200 mg of tert-butyl 4-(1-propynyl)-1,2,3,6-tetrahydropyridine-1-carboxylate prepared in 3) were dissolved in 3 ml of toluene and the solution was stirred at 120° C. for one night. The resulting solution was cooled down to room temperature, the solvent was evaporated in vacuo and the resulting residue was purified by a preparative thin-layer silica gel chromatography (hexane:ethyl acetate=2:1) to give 9.4 mg of the title compound as a white solid.

Workup

  1. temperatureThe resulting solution was cooled down to room temperature
  2. customthe solvent was evaporated in vacuo
  3. customthe resulting residue was purified by a preparative thin-layer silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-bb68f160b5d34066981798acd887dbdc
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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