Trifluoroacetic acid → 1-[3-(Trifluoromethyl)pyridin-2-yl]piperazine

HRID 1868015Notes

Reaction equation

HRID 1868015 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:23][C:20]([F:21])([F:22])[C:19]1[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60441266HCID 60441266, compound

Product 1

HCID 27777861-[3-(Trifluoromethyl)pyridin-2-yl]piperazineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a clear solution of 4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester in anhydrous dichloromethane (15 mL) was added TFA (8 mL) dropwise. The yellow solution was stirred at room temperature for 2.5 hour. Reaction was complete as determined by TLC. TFA was removed under reduced pressure. The residue was redissolved in dichloromethane (50 mL), and washed with sat. K2CO3 solution first, then washed with brine and dried over Na2SO4, filtered and concentrated down to give 1-(3-trifluoromethyl-pyridin-2-yl)-piperazine as a light yellow oil (1.19 g, 96.0% yield).

Workup

  1. customReaction
  2. customTFA was removed under reduced pressure
  3. dissolutionThe residue was redissolved in dichloromethane (50 mL)
  4. washwashed with sat. K2CO3 solution first
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated down

Sources & evidence

ORD record
ord-034b5cac2b834535b247a8ebd8094dd1
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

Loading…