3-(4-Nitrophenoxy)quinuclidine → 4-(1-Azabicyclo[2.2.2]oct-3-yloxy)aniline

HRID 1294672Notes

Reaction equation

HRID 1294672 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[N:11]12[CH2:12][CH2:13][CH:14]([CH2:15][CH2:16]1)[CH:9]([O:8][C:7]1[CH:17]=[CH:18][C:4]([NH2:1])=[CH:5][CH:6]=1)[CH2:10]2

Participants

4

Reactant 1

HCID 197854663-(4-Nitrophenoxy)quinuclidine

Product 1

HCID 196268754-(1-Azabicyclo[2.2.2]oct-3-yloxy)anilineYield 102.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 22A (1.02 g, 4.1 mmol) in MeOH (25 mL) was treated with Pd/C (Aldrich, 10%, 150 mg) under H2 at room temperature for 1.5 hours. The mixture was filtered through a short column of diatomaceous earth and the filtrate was concentrated under reduced pressure to provide the title compound (0.92 g, yield, 100%). 1H NMR (MeOH-d4, 300 MHz) δ 1.40–1.56 (m, 1H), 1.65–1.90 (m, 2H), 1.96–2.13 (m, 2H), 2.70–3.00 (m, 5H), 3.10–3.20 (m, 1H), 4.35 (m, 1H), 6.65–6.78 (m, 4H) ppm. MS (DCl/NH3) m/z 219 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-46133751a9494251b1b3a65f093427ec
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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