2-Phenylindolizine → 2-Phenyl-5,6,7,8-tetrahydroindolizine

HRID 37826Notes

Reaction equation

HRID 37826 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[N:14]([CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Ni].C(O)C>[C:1]1([C:7]2[CH:8]=[C:9]3[N:14]([CH:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 961282-Phenylindolizine

Product 1

HCID 150316492-Phenyl-5,6,7,8-tetrahydroindolizineYield 67.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

Raney nickel (6 g) was slurried in ethanol (100 mL) and a solution of 2-phenylindolizine (48 g, 0.24 mol) in ethanol (1 L) was added. The reaction mixture was stirred under hydrogen at room temperature and 50-60 psi overnight. The mixture was filtered through Celite then the solvent was evaporated under vacuum to yield 2-phenyl-5,6,7,8-tetrahydro-indolizine (32 g, 65%) as a white solid.

Workup

  1. custom50-60 psi overnight
  2. filtrationThe mixture was filtered through Celite
  3. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-a7a937471c4b4c98a4ec669f04fc0d5f
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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