Trifluoroacetic acid → HCID 9966428, compound

HRID 1005667Notes

Reaction equation

HRID 1005667 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:29]=2[NH:28][CH:27]=[C:26]3[S:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.[OH-].[NH4+]>ClCCl.O>[C:31]1([S:30][C:26]2[C:25]3[C:29](=[C:21]([N:18]4[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]4)[CH:22]=[CH:23][CH:24]=3)[NH:28][CH:27]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 60108779HCID 60108779, compound

Product 1

HCID 9966428HCID 9966428, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of 4-(3-phenylsulfanyl-1H-indol-7-yl)piperazine-1-carboxylic acid tert-butyl ester (700 mg, 1.7 mmol), prepared as described in Example 1 Step 1, in 4 mL of dichloromethane. After 15 min the solution was diluted with water, basified with ammonium hydroxide, and extracted with dichloromethane. The dichloromethane was washed with brine and evaporated to afford 3-phenylsulfanyl-7-piperazin-1-yl-1H-indole (701) as a solid. The hydrochloride salt crystallized from ethanol-HCl to afford 500 mg of white solid, m.p. 300° C. Similarly replacing 4-(3-phenylsulfanyl-1H-indol-7-yl)piperazine-1-carboxylic acid tert-butyl ester with the appropriate sulfanyl derivatives, prepared as described in other examples herein, the following compounds were prepared:

Workup

  1. customprepared
  2. extractionextracted with dichloromethane
  3. washThe dichloromethane was washed with brine
  4. customevaporated

Sources & evidence

ORD record
ord-be4cc0024ff241b6abc2466bd0c5117e
Source dataset
uspto-grants-2004_09
Patent number
US06787535B2

Reaction notes

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