Trifluoroacetic acid → Trifluoroacetylpiperazine

HRID 1023036Notes

Reaction equation

HRID 1023036 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:18][C:15]([F:16])([F:17])[C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20294522Tert-butyl 4-(2,2,2-trifluoroacetyl)piperazine-1-carboxylate

Product 1

HCID 7172020Trifluoroacetylpiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 1c (15.15 g, 53.69 mmol) in CH2Cl2 (60 mL) was added trifluoroacetic acid (18 mL) at room temperature. The mixture was stirred at room temperature for 18 h. The solvent was removed by evaporation. Ether (100 mL) was added to the residue. The white solid was collected by filtration, washed with ether, and dried under vacuum. The crude compound 1d was used in the next reaction without further purification. MS m/z (M+H+) 183.1.

Workup

  1. customThe solvent was removed by evaporation
  2. additionEther (100 mL) was added to the residue
  3. filtrationThe white solid was collected by filtration
  4. washwashed with ether
  5. customdried under vacuum
  6. customThe crude compound 1d was used in the next reaction without further purification

Sources & evidence

ORD record
ord-ded4dd7687d24841bd7e0c839e07469f
Source dataset
uspto-grants-2014_05
Patent number
US08722658B2

Reaction notes

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