Trifluoroacetic acid → 1-Biphenyl-2-ylmethyl-piperazine

HRID 410335Notes

Reaction equation

HRID 410335 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:16]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 467430664-Biphenyl-2-ylmethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 183819371-Biphenyl-2-ylmethyl-piperazineYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-biphenyl-2-ylmethyl-piperazine-1-carboxylic acid tert-butyl ester (9.89 g, 28.1 mmol) in dichloromethane (112.5 ml) at rt was added TFA (37.5 ml). The reaction was stirred for 4.5 h and then concentrated under reduced pressure. To the crude product was added H2O (20 ml) followed by 1M NaOH and then 5M NaOH to adjust the pH to ˜8-9. The mixture was extracted with dichloromethane (×2) and the combined organic extracts were washed with H2O, brine, dried (Na2SO4), filtered and concentrated under reduced pressure to provide 1-biphenyl-2-ylmethyl-piperazine (6.55 g, 92%) which was used without further purification. HPLC-MS 253 [M+1]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the crude product was added H2O (20 ml)
  3. extractionThe mixture was extracted with dichloromethane (×2)
  4. washthe combined organic extracts were washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33664e78bdff4d3a8a2b466e78d51a48
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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