HCID 67263631, compound → HCID 67263683, compound

HRID 1687064Notes

Reaction equation

HRID 1687064 reaction equation
[CH2:1]([N:3]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:5]([C:6]3[CH:7]=[CH:8][C:9]([N+:16]([O-])=O)=[CH:10][C:11]=32)[CH2:4]1)[CH3:2]>CO.[Pd]>[CH2:1]([N:3]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:5]([C:6]3[CH:7]=[CH:8][C:9]([NH2:16])=[CH:10][C:11]=32)[CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 67263631HCID 67263631, compound

Product 1

HCID 67263683HCID 67263683, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10-Ethyl-4-nitro-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2(7),3,5-triene (68 mg, 0.276 mmol) was placed in methanol (4 mL) and 10% palladium on carbon (6.8 mg) was added. The reaction was hydrogenated at 15 psi for 30 minutes. The mixture was then filtered through celite and concentrated under reduced pressure to obtain 10-ethyl-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2(7),3,5-trien-4-ylamine as a yellow oil (59.6 mg, 100%). LCMS (m/e) 217 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 6.85 (d, 1H, J=7.4 Hz), 6.50-6.45 (m, 2H), 3.52 (bs, 2H), 2.94-2.85 (m, 4H), 2.42 (q, 2H, J=7.1 Hz), 2.20-2.12 (m, 4H), 1.60-1.56 (m, 2H), 0.99 (t, 3H, J=7.1 Hz).

Workup

  1. filtrationThe mixture was then filtered through celite and
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0dee40cdfe9f42ea8f8b61f7af44ac32
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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