Water → HCID 12812497, compound

HRID 2164525Notes

Reaction equation

HRID 2164525 reaction equation
[CH3:1][CH:2]([N:9]1[CH2:12][CH:11]([O:13][C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-:22].[K+].[OH2:24].C([OH:29])(C)(C)C>>[C:14]([OH:29])(=[O:13])[C:15]([OH:24])=[O:22].[CH3:1][CH:2]([N:9]1[CH2:12][CH:11]([O:13][C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]([NH2:18])=[O:29])[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 12812495HCID 12812495, compound

Product 1

HCID 12812497HCID 12812497, compound

Procedure

3-[1-(α-Methylbenzyl)-3-azetidinyloxy]benzonitrile (50.0 g., 0.18 mole) in 500 ml of t-butyl alcohol was treated with 50.0 g. of finely ground potassium hydroxide. The mixture was stirred at reflux for 30 min. Ice and water were added to the reaction mixture and the organic layer was separated and dried over sodium sulfate. The dried filtered solution was concentrated at reduced pressure. The residue was dissolved in methanol and treated with an equivalent of oxalic acid, and the oxalate salt was recrystallized from ethanol to give 11.4 g. (16%) of product, (m.p. 145° C.).

Workup

  1. temperatureat reflux for 30 min
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationThe dried filtered solution
  5. concentrationwas concentrated at reduced pressure
  6. dissolutionThe residue was dissolved in methanol
  7. additiontreated with an equivalent of oxalic acid
  8. customthe oxalate salt was recrystallized from ethanol
  9. customto give 11.4 g

Sources & evidence

ORD record
ord-dd3bf4a64c4149de9f5da43b0718dc00
Source dataset
uspto-grants-1985_03
Patent number
US04505907

Reaction notes

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