3-[(4'-Nitro-1,1'-biphenyl-4-yl)oxy]quinuclidine → 4'-(1-Azabicyclo[2.2.2]oct-3-yloxy)-1,1'-biphenyl-4-amine

HRID 969975Notes

Reaction equation

HRID 969975 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]3[CH:22]4[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]4)[CH2:18]3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[N:19]12[CH2:20][CH2:21][CH:22]([CH2:23][CH2:24]1)[CH:17]([O:16][C:13]1[CH:12]=[CH:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)=[CH:15][CH:14]=1)[CH2:18]2

Participants

4

Reactant 1

HCID 210726053-[(4'-Nitro-1,1'-biphenyl-4-yl)oxy]quinuclidine

Product 1

HCID 113469324'-(1-Azabicyclo[2.2.2]oct-3-yloxy)-1,1'-biphenyl-4-amineYield 65.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 5A (150 mg, 0.46 mmol) in methanol (5 mL) was treated with Pd/C (Aldrich, wt. 10%, 20 mg) at ambient temperature for 30 minutes. The mixture was filtered and the filtrate was concentrated under reduced pressure to provide the title compound (89 mg, yield, 65%). 1H NMR (MeOH-d4, 300 MHz) δ 1.44-1.58 (m, 1H), 1.63-1.89 (m, 2H), 1.99-2.13 (m, 1H), 2.15-2.23 (m, 1H), 2.72-3.04 (m, 5H), 3.29-3.39 (m, 1H), 4.50-4.58 (m, 1H), 6.77 (dt, J=8.8, 2.5 Hz, 2H), 6.91 (dt, J=8.8, 2.4 Hz, 2H), 7.32 (dt, J=8.5, 2.5 Hz, 2H), 7.43 (dt,J=9.2, 2.8 Hz, 2H) ppm. MS (DCl/NH3) m/z 295 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c71a55e7276a4ef9a40a3c0e5981c23c
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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