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Trifluoroacetic acid → 1-Benzyl-4-(piperidin-4-ylcarbonyl)piperazine

HRID 2288738
Notes
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Reaction equation

HRID 2288738 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 40146251-Benzyl-4-[(1-t-butoxycarbonyl-4-piperidyl)carbonyl]piperazine

Product 1

HCID 8839341-Benzyl-4-(piperidin-4-ylcarbonyl)piperazineYield 65.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
24 °C

Procedure

A solution of 1-benzyl-4-[(1-t-butoxycarbonyl-4-piperidyl)carbonyl]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-piperidyl)carbonyl]piperazine (56.2 g, 65% yield) as a white solid;

Workup

  1. temperaturemaintaining the temperature below 25° C. under an atmosphere of argon
  2. customThe solution was evaporated
  3. customtemperature of 30° C
  4. additionThe residual oil was poured, in portions, into saturated aqueous sodium carbonate solution (770 ml)
  5. temperaturewhile maintaining the temperature below 30° C
  6. extractionThe aqueous mixture was extracted with dichloromethane (3×575 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-0c3d6463bb284a77bac6eb3b620387a6
Source dataset
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06090813

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes