Potassium Hydroxide → 3',4'-dihydro-2-oxospiro[piperidine-4,4'(1H)-quinoline]

HRID 1735469Notes

Reaction equation

HRID 1735469 reaction equation
F[C:2](F)(F)[C:3]([NH2:5])=[O:4].[NH:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)C(=O)C2)[CH2:10][CH2:9]1.[OH-].[K+]>CO.O>[O:4]=[C:3]1[CH2:2][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:8][CH2:9][CH2:10]2)[CH2:12][CH2:13][NH:5]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18467060Spiro[1H-indene-1,4'-piperidin]-3(2H)-one trifluoroacetamide

Product 1

HCID 677074473',4'-dihydro-2-oxospiro[piperidine-4,4'(1H)-quinoline]Yield 91.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 49 mg (0.157 mmol) of the high RF material from Step B in methanol/water 4:1 with excess potasium hydroxide was stirred over night. The solution was concentrated and water and ethyl acetate were added to the residue. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to give 31 mg (0.143 mmol) of the title compound.

Workup

  1. concentrationThe solution was concentrated
  2. additionwater and ethyl acetate were added to the residue
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c0cc39d81fea46c8b46bb56cb782ca50
Source dataset
uspto-grants-1996_07
Patent number
US05536716

Reaction notes

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