Trifluoroacetic acid → 1-[3-(1-Pyrrolidinyl)-2-pyridinyl]piperazine

HRID 2293746Notes

Reaction equation

HRID 2293746 reaction equation
CC(C)(OC([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=O)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C1COCC1>[N:19]1([C:18]2[C:13]([N:10]3[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]3)=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 214776341-[1,1-Dimethylethoxycarbonyl]-4-[3-(1-pyrrolidinyl)-2-pyridinyl]piperazine

Product 1

HCID 214776301-[3-(1-Pyrrolidinyl)-2-pyridinyl]piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[1,1-Dimethylethoxycarbonyl]-4-[3-(1-pyrrolidinyl)-2-pyridinyl]piperazine (PREPARATION 16, 0.26 g) is dissolved in 1.3 ml of THF and cooled to 0°. Trifluoroacetic acid (1.3 ml) is added and the reaction is stirred at 0° for 20 min, and then warmed to 20°-25° for 20 min. Then the reaction is poured into 1N aqueous sodium hydroxide and extracted with methanol/chloroform (10/90, 2×50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound, NMR (300 MHz, CDCl3) 7.64, 6.81, 6.61, 3.05-2.94, 2.86-2.79 and 1.78-1.65 δ.

Workup

  1. temperaturecooled to 0°
  2. temperaturewarmed to 20°-25° for 20 min
  3. extractionextracted with methanol/chloroform (10/90, 2×50 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bae0472c46dd47c78d55a65ec2950753
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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