Potassium Iodide → 1'-(2-Phenoxyethyl)-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine hydrochloride

HRID 224612

Reaction equation

HRID 224612 reaction equation
[O:1]([CH2:8][CH2:9][Cl:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][N:12]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:13]1=[O:26].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[ClH:10].[O:1]([CH2:8][CH2:9][N:17]1[CH2:18][CH2:19][C:14]2([C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:12]([CH3:11])[C:13]2=[O:26])[CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12156Benzene, (2-chloroethoxy)-HCID 215841551-Methylspiro[indoline-3,4'-piperidin]-2-one

Product 1

HCID 705944601'-(2-Phenoxyethyl)-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.63 g of phenoxyethylchloride, 1.5 g of 1-methyl-2-oxo-indoline-3-spiro-4'-piperidine, 1.44 g of anhydrous potassium carbonate, 0.1 g of potassium iodide and 30 ml of dimethylformamide was stirred at 90°-100° C. for 5 hours. The resulting mixture was poured into water and was extracted with diethylether. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Thus obtained oil was treated with hydrochloric acid to give 1'-(2-phenoxyethyl)-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine hydrochloride

Workup

  1. extractionwas extracted with diethylether
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. additionThus obtained oil was treated with hydrochloric acid

Sources & evidence

ORD record
ord-c453dcfec0cf41048b5306cdb9a7f3c2
Source dataset
uspto-grants-1980_11
Patent number
US04233307

Linked notes

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