Fumaric Acid → (+/-)-3-(3-Pyridyl)-2-azabicyclo[2.2.2]octane fumarate

HRID 581817Notes

Reaction equation

HRID 581817 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH:12]3[CH2:13][CH2:14][CH:9]([CH2:10][CH2:11]3)[NH:8]2)[CH:2]=1.[C:15]([OH:22])(=[O:21])/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19]>C(O)C>[C:15]([OH:22])(=[O:21])/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH:12]3[CH2:13][CH2:14][CH:9]([CH2:10][CH2:11]3)[NH:8]2)[CH:2]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 15383498HCID 15383498, compound

Product 1

HCID 23365581(+/-)-3-(3-Pyridyl)-2-azabicyclo[2.2.2]octane fumarateYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of compound (XIII) (100 mg, 0.531 mmol) in absolute ethanol (5 mL) was added fumaric acid (124 mg, 1.062 mmol). The resulting suspension was sonicated until complete dissolution occurred. The solvent was removed on rotary evaporator to give a colorless syrup which was crystallized from absolute ethanol to yield 156 mg (70%) of compound (XIV). Mp=180° C. (decomposition). 1H NMR(D2O, TSP): δ 8.80 (br s,2H), 8.40(d, 1H),7.95, (s, 1H),6.70 (s,2H), 5.08 (s, 1H), 4.21 (s, 1H), 3.08 (s, 1H), 2.40 (m, 1H), 2.02-1.60 (m, 8H).

Workup

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

Sources & evidence

ORD record
ord-985340d0aac5454198bc4f9bc3cf529c
Source dataset
uspto-grants-1999_07
Patent number
US05922723

Reaction notes

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