Trifluoroacetic acid → 1-(6-Bromopyridin-3-yl)piperazine

HRID 2246213Notes

Reaction equation

HRID 2246213 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1>ClCCl>[Br:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11530243Tert-butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 98780901-(6-Bromopyridin-3-yl)piperazineYield 141.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.20 ml (150.77 mmol) of trifluoroacetic acid are slowly added to a suspension of 5.16 g (15.08 mmol) of 1,1-dimethylethyl 4-(6-bromo-3-pyridyl)-1-piperazine-carboxylate, obtained in step 7.2., in 70 ml of dichloromethane. Stirring is continued at room temperature for 16 hours. The reaction mixture is concentrated under reduced pressure, the residue is taken up in 40 ml of chloroform and 4 ml of aqueous sodium hydroxide solution (10M) are then slowly added. The aqueous phase is separated out and then extracted twice with chloroform. The organic phases are combined and are washed with saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulfate and the filtrate is concentrated under reduced pressure. 5.16 g of product are thus obtained in the form of an orange-colored oil that crystallizes at room temperature. This product is used without further purification in the following step.

Workup

  1. customobtained in step 7.2
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. addition4 ml of aqueous sodium hydroxide solution (10M) are then slowly added
  4. customThe aqueous phase is separated out
  5. extractionextracted twice with chloroform
  6. washare washed with saturated aqueous sodium chloride solution
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-ad7362581ad242a49ee5bb0f12502342
Source dataset
uspto-grants-2010_03
Patent number
US07687503B2

Reaction notes

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