HCID 67263778, compound → HCID 67264192, compound

HRID 1687068Notes

Reaction equation

HRID 1687068 reaction equation
[CH:1]([N:4]1[CH2:14][CH:13]2[CH2:15][CH2:16][CH:6]([C:7]3[CH:8]=[CH:9][C:10]([N+:17]([O-])=O)=[CH:11][C:12]=32)[CH2:5]1)([CH3:3])[CH3:2]>CO.[Pd]>[CH:1]([N:4]1[CH2:14][CH:13]2[CH2:15][CH2:16][CH:6]([C:7]3[CH:8]=[CH:9][C:10]([NH2:17])=[CH:11][C:12]=32)[CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67263778HCID 67263778, compound

Product 1

HCID 67264192HCID 67264192, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10-Isopropyl-4-nitro-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2(7),3,5-triene (62 mg, 0.238 mmol) was placed in methanol (4 mL) and 10% palladium on carbon (6.2 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-isopropyl-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2(7),3,5-trien-4-ylamine as a yellow oil (54.7 mg, 100%). LCMS (m/e) 231 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 6.85 (dd, 1H, J=0.7 and 7.2 Hz), 6.50-6.45 (m, 2H), 3.52 (bs, 2H), 2.87-2.78 (m, 5H), 2.33-2.26 (m, 2H), 2.18-2.09 (m, 2H), 1.60-1.50 (m, 2H), 0.93 (d, 6H, J=6.6 Hz).

Workup

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

Sources & evidence

ORD record
ord-41872294c9cd4379bdac92ee0d155681
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

Loading…