Fumaric Acid → (+/-)-2-Methyl-3-(3-pyridyl)-2-azabicyclo[2.2.2]octane Fumarate

HRID 1080680Notes

Reaction equation

HRID 1080680 reaction equation
[CH3:1][N:2]1[CH:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:6]2[CH2:14][CH2:15][CH:3]1[CH2:4][CH2:5]2.[C:16]([OH:23])(=[O:22])/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20]>C(O)C>[C:16]([OH:23])(=[O:22])/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20].[CH3:1][N:2]1[CH:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:6]2[CH2:14][CH2:15][CH:3]1[CH2:4][CH2:5]2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 18694214HCID 18694214, compound

Product 1

HCID 23365584(+/-)-2-Methyl-3-(3-pyridyl)-2-azabicyclo[2.2.2]octane FumarateYield 120.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of compound (XV) (1 20 mg, 0.495 mmol) in absolute ethanol (5 mL) was added fumaric acid (138 mg, 1.18 mmol). The resulting suspension was sonicated until complete dissolution occurred. The solvent was removed on a rotary evaporator to give a colorless syrup which was crystallized from absolute ethanol to yield 190 mg (88%) of compound (XVI). Mp=142°-143° C.

Workup

  1. customThe resulting suspension was sonicated until complete dissolution
  2. customThe solvent was removed on a rotary evaporator
  3. customto give a colorless syrup which
  4. customwas crystallized from absolute ethanol

Sources & evidence

ORD record
ord-502c8a6ce8f0483faf141913582b8567
Source dataset
uspto-grants-1996_12
Patent number
US05583140

Reaction notes

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