Water → 5-Azido-5,6,7,8-tetrahydroquinoxaline

HRID 1624311Notes

Reaction equation

HRID 1624311 reaction equation
Br[CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[CH:6][CH:5]=[N:4][C:3]1=2.[N-:12]=[N+:13]=[N-:14].[Na+].O>CN(C=O)C>[N:12]([CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[CH:6][CH:5]=[N:4][C:3]1=2)=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 177500155-Bromo-5,6,7,8-tetrahydroquinoxaline

Product 1

HCID 581494935-Azido-5,6,7,8-tetrahydroquinoxalineYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

5-bromo-5,6,7,8-tetrahydroquinoxaline (2.75 g, 12.9 mmol) and sodium azide (1.68 g, 25.8 mmol) were dissolved in DMF (50 mL) under nitrogen atmosphere and the reaction mixture was warmed to 60° C. for 2 days. The mixture was cooled to room temperature and poured over water (500 mL), and was extracted with CH2Cl2 (3×300 mL). The organic extracts were washed with brine (2×200 mL), dried and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel using 1:1 EtOAc/hexanes to afford 2.19 g (97%) of 5-azido-5,6,7,8-tetrahydroquinoxaline as a yellow liquid: 1H NMR (CDCl3): δ 1.80-1.96 (m, 1H), 2.00-2.10 (m, 3H), 2.75-3.06 (m, 2H), 4.74 (t, 1H, J=6.5 Hz), 8.44 (d, 1H, J=3 Hz), 8.45 (d, 1H, J=3 Hz); 13C NMR (CDCl3): δ 18.6, 28.9, 31.7, 60.2, 142.6, 144.3, 150.3, 153.6.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionwas extracted with CH2Cl2 (3×300 mL)
  3. washThe organic extracts were washed with brine (2×200 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography on silica gel using 1:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-21a092d4393743d19941340b9a8e3d43
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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