Trifluoroacetic acid → 1-Benzyl-4-(piperidin-4-ylcarbonyl)piperazine
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 24 °C
Procedure
A solution of l-benzyl-4-[1-(t-butoxycarbonyl)-4-piperidylcarbonyl]piperazine (115.7 g) in dry dichloromethane (222 ml) was added dropwise over 45 minutes to trifluoroacetic acid (575 ml), maintaining the temperature below 25° C. under an atmosphere of argon. The solution was stirred at 23-25° C. for 1 hour. The solution was evaporated using a bath temperature of 30° C. The residual oil was poured, in portions, into saturated aqueous sodium carbonate solution (770 ml) while maintaining the temperature below 30° C. The aqueous mixture was extracted with dichloromethane (3×575 ml). The dichloromethane extracts were combined, dried (Na2SO4) and evaporated to give 1-benzyl-4-(4-piperidylcarbonyl)piperazine (56.2 g, 65% yield) as a colourless solid;
Workup
- temperaturemaintaining the temperature below 25° C. under an atmosphere of argon
- customThe solution was evaporated
- customtemperature of 30° C
- additionThe residual oil was poured, in portions, into saturated aqueous sodium carbonate solution (770 ml)
- temperaturewhile maintaining the temperature below 30° C
- extractionThe aqueous mixture was extracted with dichloromethane (3×575 ml)
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-535cf444866a4227a487a90320dc9ea6
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06093718
Reaction notes
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