3-(2-Pyrazinyl)-1-azabicyclo[2.2.2]oct-2-ene → 3-Pyrazin-2-yl-1-aza-bicyclo[2.2.2]octane

HRID 256871Notes

Reaction equation

HRID 256871 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:12]2[CH2:13][CH2:14][N:9]([CH2:10][CH2:11]2)[CH:8]=1>C(O)C>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH:7]1[CH:12]2[CH2:13][CH2:14][N:9]([CH2:10][CH2:11]2)[CH2:8]1

Participants

3

Reactant 1

HCID 157501423-(2-Pyrazinyl)-1-azabicyclo[2.2.2]oct-2-ene

Product 1

HCID 157501533-Pyrazin-2-yl-1-aza-bicyclo[2.2.2]octaneYield 72.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(2-pyrazinyl)-1-azabicyclo [2.2.2]-oct-2-ene (75 mg, 0.4 mmol), in ethanol (20 ml), was hydrogenated over 10% pd/C (75 mg) in a Parr apparatus. After 1.5 h the catalyst was removed by filtration through hyflo and the solvent removed under reduced pressure. Chromatography of the residue through alumina eluting with dichloromethane/methanol (95:5) gave 3-(2-pyrazinyl)-1-azabicyclo [2.2.2]octane (55 mg) as a pale yellow oil. The hydrochloride salt was prepared, m.p. 203°-205° C. (isopropyl alcohol/ether); (Found C, 55.23; H, 7.15; N, 17.86 C11H15N3. HCl. 0.75 H2O requires C, 55.23; H, 7.32: N, 17.57%); m/e 189 (M+ for free base); δ (360 MHz, D2O) 1.70-1.85 (2H, m, CH2); 2.10-2.30 (2H, m, CH2); 2.40-2.48 (1H, m, CH-bridgehead); 3.28-4.04 (7H, m, 3×CH2 and CH); 8.52 (1H, m, pyrazine-H); 8.63 (2H, m, pyrazine-H).

Workup

  1. customAfter 1.5 h the catalyst was removed by filtration through hyflo
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-464f9eb28bbb423dbd4cb80a7b7a597f
Source dataset
uspto-grants-1993_11
Patent number
US05260293

Reaction notes

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