Trifluoroacetic acid → HCID 70565525, compound

HRID 1155578Notes

Reaction equation

HRID 1155578 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]1)=[CH:8][C:7]([C:25]([F:28])([F:27])[F:26])=[CH:6][CH:5]=2.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.[OH-].[Na+]>>[CH3:1][C@H:2]1[C@@H:10]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:17][CH2:18]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:25]([F:28])([F:26])[F:27])[CH:8]=2)[NH:3]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 20561386HCID 20561386, compound

Product 1

HCID 70565525HCID 70565525, compound

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 1.2 g. of the product of Example 12 and 30 ml. of trifluoroacetic acid, heated to 50° C. is added 3.0 ml. of triethylsilane. This solution is stirred and heated at 50° C. for 96 hours. The reaction mixture is poured onto chopped ice and 50 ml. of 10 N sodium hydroxide. Then the aqueous mixture is extracted with chloroform. The chloroform solution is dried over magnesium sulfate and concentrated under reduced pressure to yield cis-2-methyl-5-trifluoromethyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]indoline as the product. This compound is dissolved in ethyl acetate and acidified with anhydrous hydrogen chloride. The solid which precipitates is collected by filtration to provide the desired cis indoline dihydrochloride as the product of the Example.

Workup

  1. additionis added 3.0 ml
  2. additionThe reaction mixture is poured
  3. extractionThen the aqueous mixture is extracted with chloroform
  4. dry with materialThe chloroform solution is dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cc0cb55aafdb403889affd7b85cccec9
Source dataset
uspto-grants-1981_11
Patent number
US04302589

Reaction notes

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