Sodium Hydroxide → HCID 54491573, compound

HRID 567776Notes

Reaction equation

HRID 567776 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][N:2]2[C:9](=[O:27])[C:10]([C:13]1[N:18]=[CH:17][C:16]([NH:19]C(=O)C(C)(C)C)=[C:15]([I:26])[CH:14]=1)([CH3:12])[CH3:11].[OH-].[Na+]>OS(O)(=O)=O>[NH2:19][C:16]1[C:15]([I:26])=[CH:14][C:13]([C:10]([CH3:11])([CH3:12])[C:9]([N:2]2[CH2:3][CH:4]3[CH2:7][CH2:8][CH:1]2[CH2:6][CH2:5]3)=[O:27])=[N:18][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21262714HCID 21262714, compound

Product 1

HCID 54491573HCID 54491573, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A vigorously stirred mixture of N-{6-[2-(2-azabicyclo[2.2.2] oct-2-yl)-1,1-dimethyl-2-oxoethyl]-4-iodopyridin-3-yl}-2,2-dimethyl-propionamide (4.66 g, 9.64 mmol.) in 24% H2SO4 (48 mL) was heated at 100° C. for approximately 3.5h. After cooling to room temperature, the reaction mixture was basified to pH=10 with 2.5N NaOH and then extracted with ethyl acetate (×3). The combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by recrystallization from dichloromethane/diethyl ether to give the title compound as prisms (3.02 g, 78%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (×3)
  3. extractionThe combined organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by recrystallization from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-20f949754151492b8a9c23bb8661babd
Source dataset
uspto-grants-2001_01
Patent number
US06180642B2

Reaction notes

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