Trifluoroacetic acid → HCID 14881723, compound

HRID 704442Notes

Reaction equation

HRID 704442 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH:14]2[NH:18][CH:17]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:23][CH2:22]3)=[O:20])[CH2:16][S:15]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[C:30]1([CH2:29][CH2:28][CH2:27][N:24]2[CH2:25][CH2:26][N:21]([C:19]([CH:17]3[CH2:16][S:15][CH:14]([CH:10]4[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]4)[NH:18]3)=[O:20])[CH2:22][CH2:23]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 14881571HCID 14881571, compound

Product 1

HCID 14881723HCID 14881723, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[2-(1-tert-Butoxycarbonyl-3-piperidinyl)thiazolidin-4-ylcarbonyl]-4-(3-phenylpropyl)piperazine (430 mg) was dissolved in 3 ml of dichloromethane, followed by addition of 2 ml of trifluoroacetic acid. The mixture was stirred at room temperature for 6 hours. The reaction mixture was poured into 60 ml of saturated aqueous solution of sodium hydrogen carbonate, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 280 mg of 1-(3-phenylpropyl)-4-[2-(3-piperidinyl)thiazolidin-4-ylcarbonyl]piperazine. This compound was dissolved in 8 ml of ethyl acetate, and 1 ml of 4N hydrogen chloride solution in dioxane was added. After 30 minutes of stirring, the resultant solid was collected by filtration and dried to give 200 mg of 1-(3-phenylpropyl)-4-[2-(3-piperidinyl)thiazolidin-4-ylcarbonyl]piperazine trihydrochloride. Melting point 174°-178° C.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cdf0402948b14bdbbd6109a4dd45a1b0
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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