HCID 86590306, compound → HCID 12099066, compound

HRID 1624255Notes

Reaction equation

HRID 1624255 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, by 105-140° C. @ 0.2 Ton) 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, by 105-140° C. @ 0.2 Ton)

Sources & evidence

ORD record
ord-b2794661a95743dc9e05c359e8c4c799
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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