Trifluoroacetic acid → 1-(4-Pyridylpiperidin-4-ylcarbonyl)piperazine

HRID 2288733Notes

Reaction equation

HRID 2288733 reaction equation
C(O[N:6]1[CH2:11][CH2:10][N:9]([C:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH2:8][CH2:7]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:23]1[CH:22]=[CH:21][C:20]([N:17]2[CH2:18][CH2:19][CH:14]([C:12]([N:9]3[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]3)=[O:13])[CH2:15][CH2:16]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 187002554-(t-Butoxy)-1-(4-pyridylpiperidin-4-ylcarbonyl)piperazine

Product 1

HCID 108022941-(4-Pyridylpiperidin-4-ylcarbonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The 4-(t-butoxy)-1-(4-pyridylpiperidin-4-ylcarbonyl)piperazine (3.74 g) was then dissolved in dry dichloromethane (50 ml) and treated with trifluoroacetic acid (5.3 ml) and stirred under an argon atmosphere at room temperature for three hours. The dichloromethane solvent was then removed by evaporation to afford a brown oil which slowly solidified, This solid was then taken up in dichloromethane, filtered and washed with water, brine and then dried (MgSO4). The resultant solution was then evaporated to dryness to yield a pale yellow oil which slowly crystallised to give 1-(4-pyridylpiperidin-4-ylcarbonyl)piperazine as a yellow solid;

Workup

  1. customThe dichloromethane solvent was then removed by evaporation
  2. customto afford a brown oil which
  3. filtrationfiltered
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customThe resultant solution was then evaporated to dryness
  7. customto yield a pale yellow oil which
  8. customslowly crystallised

Sources & evidence

ORD record
ord-aee5f7c9831a4101a21ddde95bcb4c50
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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