HCID 18966441, compound → HCID 18966405, compound

HRID 2226148Notes

Reaction equation

HRID 2226148 reaction equation
Cl.Cl.[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]2[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]2)[CH:10]=1>CO.[Pd]>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH:14]2[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]2)[CH2:10]1

Participants

4

Reactant 1

HCID 18966441HCID 18966441, compound

Product 1

HCID 18966405HCID 18966405, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(2-pyridinyl)-1-azabicyclo[2.2.2]oct-2-ene dihydrochloride (0.28 g, prepared as in Example 5) in methanol (10 ml) was hydrogenated over 10% palladium on carbon (20 mg) in a Parr apparatus at 45 psi for 1 h. The suspension was filtered and concentrated. The crude product was recrystallised from methanol/ether to give 81 mg of the title compound as the dihydrochloride salt; m.p. 180°-190° C.; Found: C, 53.70; H, 7.04; N, 10.47. C12H18N2Cl2. 0.35 H2O requires C, 53.88; H, 7.05; N, 10.47; δ(360 MHz, D2O) 8.738 (1H, d, J=5.6 Hz, py-H), 8.555 (1H, t, J=8.0 Hz, py-H), 8.086 (1H, d, J=8.2 Hz, py-H), 7.934 (1H, t, J=6.5 Hz, py-H), 4.00- 3.75 (3H, m, H2 -2 and H-3), 3.60-3.30 (4H, m, H2 -6 and H2 -7) 2.54 (1H, m, H-4), 2.30-1.80 (4H, m, H2 -5 and H2 -8); m/e 188 (M+).

Workup

  1. filtrationThe suspension was filtered
  2. concentrationconcentrated
  3. customThe crude product was recrystallised from methanol/ether

Sources & evidence

ORD record
ord-c41c1635748c4c5b87d8165ab4232ac0
Source dataset
uspto-grants-1994_09
Patent number
US05346906

Reaction notes

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