HCID 53673921, compound → HCID 15383498, compound

HRID 581816Notes

Reaction equation

HRID 581816 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)[N:8]2C(OCC)=O)[CH:2]=1>[OH-].[Na+].C(O)C>[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 1

HCID 53673921HCID 53673921, compound

Product 1

HCID 15383498HCID 15383498, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

(+/-)-3-(3-pyridyl)-2-carboethoxy-2-azabicyclo[2.2.2]octane (XII) (500 mg, 1.92 mmol) was dissolved in a solution of 20% (w/v) NaOH in absolute ethanol (10 mL) and refluxed for 24 h. The organic solvent was evaporated on a rotary evaporator. The pH of the basic residue was adjusted to 9 by addition of a solution of 2N HCl in water and was extracted with ethyl acetate (4×10 mL). The organic extracts were dried over anhydrous K2CO3, and concentrated. The resulting oily residue was purified by distillation under reduced pressure (108°-110° C./0.4 mm Hg) to afford 300 mg (83%) of compound (XIII). 1H NMR (CDCl3): δ 8.62-8.61 (d, 1H), 8.44-8.41 (m, 1H), 7.80-7.72 (m, 1H), 7.24-7.21 (m, 1H), 4.30 (s, 1H), 3.71-3.63(m, 1H), 2.20(m, 1H), 2.0-1.51 (m, 8H), 1.42 (d, 1H).

Workup

  1. temperaturerefluxed for 24 h
  2. customThe organic solvent was evaporated on a rotary evaporator
  3. additionThe pH of the basic residue was adjusted to 9 by addition of a solution of 2N HCl in water
  4. extractionwas extracted with ethyl acetate (4×10 mL)
  5. dry with materialThe organic extracts were dried over anhydrous K2CO3
  6. concentrationconcentrated
  7. distillationThe resulting oily residue was purified by distillation under reduced pressure (108°-110° C./0.4 mm Hg)

Sources & evidence

ORD record
ord-87e72b15bef14fbf949d38a58964300a
Source dataset
uspto-grants-1999_07
Patent number
US05922723

Reaction notes

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