Trifluoroacetic acid → 1-(5-(2-(Piperazin-1-yl)ethyl)indolin-1-yl)ethanone

HRID 535649

Reaction equation

HRID 535649 reaction equation
FC(F)(F)C(O)=O.[C:8]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)(=[O:10])[CH3:9]>C(Cl)Cl>[N:22]1([CH2:21][CH2:20][C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[N:11]([C:8](=[O:10])[CH3:9])[CH2:12][CH2:13]3)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59636762Tert-butyl 4-(2-(1-acetylindolin-5-yl)ethyl)piperazine-1-carboxylate

Product 1

HCID 596367471-(5-(2-(Piperazin-1-yl)ethyl)indolin-1-yl)ethanoneYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4.08 mL, 53.08 mmol) was added to a solution of tert-butyl 4-(2-(1-acetylindolin-5-yl)ethyl)piperazine-1-carboxylate (0.793 g, 2.12 mmol) in dry DCM and the reaction was stirred at room temperature for 60 min. The mixture was evaporated and the crude mixture was made basic with 10% NaOH aq. The aq phase was extracted with DCM (3×), dried (Na2SO4), filtered and evaporated to give 0.590 g of the product. This product was taken to the next step assuming quantitative yield without further purification. MS (ES+) m/z 274.2 (M+H)+.

Workup

  1. customThe mixture was evaporated
  2. extractionwas extracted with DCM (3×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-385d2204b28b418eb06835bd6ce6981d
Source dataset
uspto-grants-2014_10
Patent number
US08859534B2

Linked notes

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