Benzyl 4-[5-(1-azabicyclo[2.2.2]oct-3-yloxy)pyrazin-2-yl]phenylcarbamate → 4-[5-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrazin-2-yl]aniline

HRID 969989Notes

Reaction equation

HRID 969989 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22]C(=O)OCC4C=CC=CC=4)=[CH:18][CH:17]=3)=[N:14][CH:15]=1)[CH2:2]2>C(O)C.[Pd]>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[N:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[N:14][CH:15]=1)[CH2:2]2

Participants

4

Reactant 1

HCID 69434813Benzyl 4-[5-(1-azabicyclo[2.2.2]oct-3-yloxy)pyrazin-2-yl]phenylcarbamate

Product 1

HCID 113470034-[5-(1-Azabicyclo[2.2.2]oct-3-yloxy)pyrazin-2-yl]anilineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product of Example 13A (0.68 g, 1.58 mmol) in ethanol (20 mL) was treated with Pd/C (Aldrich, 10% wt., 70 mg) under H2 at ambient temperature for 4 hours. The mixture was filtered through a short column of diatomaceous earth and the filtrate was concentrated to give the title product as a solid (400 mg, yield, 86%). 1H NMR (MeOH-d4, 300 MHz) δ 1.47-1.62 (m, 1H), 1.64-1.90 (m, 2H), 1.97-2.12 (m, 1H), 2.19-2.27 (m, 1H), 2.73-3.03 (m, 5H), 3.34-3.44 (m, 1H), 5.07-5.14 (m, 1H), 6.78 (dt, J=8.8, 2.7 Hz, 2H), 7.68 (dt, J=8.5, 2.7 Hz, 2H), 8.17 (d, J=1.4 Hz, 1H), 8.45 (d, J=1.4 Hz, 1H) ppm. MS (DCl/NH3) m/z 297 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a short column of diatomaceous earth
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6345ca757a564552949e57404d20ef0c
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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