Sodium Azide → HCID 86590306, compound

HRID 1624254Notes

Reaction equation

HRID 1624254 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:11](OC(=O)C)[C:2]=12.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C>[N:16]([CH:11]1[C:2]2=[N:1][CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10]1)=[N+:17]=[N-:18]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 10081676HCID 10081676, compound

Product 1

HCID 86590306HCID 86590306, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

This ester was dissolved in DMF (420 mL), treated with sodium azide (33.40 g, 0.514 mol), and heated at 60° C. overnight. The mixture was cooled to room temperature and concentrated. The resultant slurry was poured into brine (500 mL) and extracted with ether (4×500 mL). The combined organic extracts were washed with brine (2×100 mL), dried (Na2SO4), and concentrated. The crude material was filtered (eluant CH2Cl2) through a short plug of silica gel to provide 23.18 g (42% from 2,3-cycloheptenopyridine) of 9-azido-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine as a red oil. 1H NMR (CDCl3) δ 1.53-1.66 (m, 1H), 1.73-2.14 (m, 5H), 2.63-2.72 (m, 1H), 2.99-3.09 (m, 1H), 4.93 (dd, 1H, J=7.8, 1.7 Hz), 7.13 (dd, 1H, J=7.9, 4.8 Hz), 7.44 (d, 1H, J=5.7 Hz), 8.39 (dd, 1H, J=4.8, 1.9 Hz).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additionThe resultant slurry was poured into brine (500 mL)
  4. extractionextracted with ether (4×500 mL)
  5. washThe combined organic extracts were washed with brine (2×100 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. filtrationThe crude material was filtered (eluant CH2Cl2) through a short plug of silica gel

Sources & evidence

ORD record
ord-fbcb2ab51059482eb4c263a1b7dc5cfd
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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