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

HRID 1870798Notes

Reaction equation

HRID 1870798 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) (120 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-6ea98064f1e5456f9afb8970838ed318
Source dataset
uspto-grants-2000_08
Patent number
US06100269

Reaction notes

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