Benzene, 1-fluoro-2-(trifluoromethyl)- → HCID 12801619, compound

HRID 1660353Notes

Reaction equation

HRID 1660353 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.[H-].[Na+].F[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]([F:29])([F:28])[F:27].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34]>CS(C)=O.O.CCOCC>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].[Cl:1][C:2]1[CH:7]=[C:6]2[N:8]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])[CH2:9][C:10]3([CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 9807Benzene, 1-fluoro-2-(trifluoromethyl)-HCID 24758Sodium hydrideHCID 444266Maleic AcidHCID 128016176-Chloro-1'-methylspiro[indoline-3,4'-piperidine]

Product 1

HCID 12801619HCID 12801619, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

A mixture of 2.4 g of 6-chloro-1'-methylspiro[indoline-3,4'-piperidine], 0.5 g of sodium hydride and 6 g of 2-fluorobenzotrifluoride in 30 ml of dimethylsulfoxide is stirred under nitrogen for 30 minutes. An exothermic reaction occurs during this time. Thereafter, the mixture is diluted with water, and the diluted mixture thrice with ether. The combined ether extracts are extracted with 2 N hydrochloric acid. The acidic extracts are basified providing a colorless oil. The oil is dissolved in ether and the solution is dried. The product is passed through an alumina column, ether eluant, to provide a colorless oil which is converted, in ether, to its maleic acid salt. The salt is recrystallized from an acetone-ether mixture to provide white platelets, mp 209°-211° C. of 6-chloro-1-(2-trifluoromethylphenyl)-1'-methylspiro[indoline-3,4'-piperidine] maleate.

Workup

  1. customAn exothermic reaction
  2. extractionThe combined ether extracts are extracted with 2 N hydrochloric acid
  3. customThe acidic extracts are basified providing a colorless oil
  4. customthe solution is dried
  5. customto provide a colorless oil which
  6. customThe salt is recrystallized from an acetone-ether mixture

Sources & evidence

ORD record
ord-e4131ebaa6664d84bf43b9e2319847c3
Source dataset
uspto-grants-1981_12
Patent number
US04307235

Reaction notes

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