HCID 86590306, compound → HCID 12099066, compound

HRID 899756Notes

Reaction equation

HRID 899756 reaction equation
[N:1]([CH:4]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5]1)=[N+]=[N-]>CO.[Pd]>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([NH2:1])[C:10]=12

Participants

4

Reactant 1

HCID 86590306HCID 86590306, compound

Product 1

HCID 12099066HCID 12099066, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the azide (23.18 g, 0.123 mol) in methanol (150 mL) was added Palladium, 10 wt. % on activated carbon (1.95 g) and the resultant mixture was hydrogenated at 40 psi on a Parr shaker. The mixture was vacuum filtered through celite and the cake was washed with methanol. The solvent was removed from the filtrate under reduced pressure and the oil obtained was distilled (Kugelrohr, bp 105-140° C. @ 0.2 Torr) to provide 17.56 g (88%) of 6,7,8,9-Tetrahydro-5H-cyclohepta[b]pyridin-9-ylamine as a pale yellow oil. 1H NMR (CDCl3) δ 1.23-1.37 (m, 1H), 1.43-1.57 (m, 1H), 1.78-2.10 (m, 6H) including 2.04 (s, 2H), 2.71-2.85 (m, 2H), 4.19 (dd, 1H, J=10.0, 1.5), 7.05 (dd, 1H, J=7.4, 4.9 Hz), 7.36 (d, 1H, J=5.9 Hz), 8.38 (d, 1H, J=4.9 Hz).

Workup

  1. filtrationfiltered through celite
  2. washthe cake was washed with methanol
  3. customThe solvent was removed from the filtrate under reduced pressure
  4. customthe oil obtained
  5. distillationwas distilled (Kugelrohr, bp 105-140° C. @ 0.2 Torr)

Sources & evidence

ORD record
ord-dbc196fc6f9c4ac4bebd46f7c8b6b1a4
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

Loading…