Potassium Iodide → 1'-[3-(4-Fluorobenzoyl)propyl]-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine

HRID 224611Notes

Reaction equation

HRID 224611 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:9]CCO1.[CH3:17][N:18]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[C:19]1=[O:32].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[F:16][C:13]1[CH:12]=[CH:11][C:10]([C:5]([CH2:4][CH2:3][CH2:2][N:23]2[CH2:24][CH2:25][C:20]3([C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:18]([CH3:17])[C:19]3=[O:32])[CH2:21][CH2:22]2)=[O:9])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27237782-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolaneHCID 215841551-Methylspiro[indoline-3,4'-piperidin]-2-one

Product 1

HCID 705923161'-[3-(4-Fluorobenzoyl)propyl]-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.0 g of 4-chloro-1-(4-fluorophenyl)-1,1-ethylenedioxybutane, 2.0 g of 1-methyl-2-oxo-indoline-3-spiro-4'-piperidine, 2.8 g of anhydrous potassium carbonate, 0.1 g of potassium iodide and 30 ml of dimethylformamide was refluxed for 2 hours. The resulting mixture was poured into water and was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. To the residual oil were added 60 ml of methanol, 20 ml of water and 10 ml of concentrated hydrochloric acid. The mixture was refluxed for 25 minutes and concentrated in vacuo. The residual oil was made alkaline with 28% aqueous ammonia and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated. The residual oil was chromatographed over silica gel with ethyl acetate as an elueting agent to give 1'-[3-(4-fluorobenzoyl)propyl]-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine, M.P. 95°-96.5° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. additionTo the residual oil were added 60 ml of methanol, 20 ml of water and 10 ml of concentrated hydrochloric acid
  7. temperatureThe mixture was refluxed for 25 minutes
  8. concentrationconcentrated in vacuo
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customThe residual oil was chromatographed over silica gel with ethyl acetate as an elueting agent

Sources & evidence

ORD record
ord-9ae4a1c19e7b4a739b433df2aacfd6d7
Source dataset
uspto-grants-1980_11
Patent number
US04233307

Reaction notes

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