Trifluoroacetic acid → [(2S)-2-Methyl-1-piperazinyl]phenylmethanone

HRID 1689959Notes

Reaction equation

HRID 1689959 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][C@@H:10]1[CH3:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:22][C@H:10]1[CH2:11][NH:12][CH2:13][CH2:14][N:9]1[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57581556HCID 57581556, compound

Product 1

HCID 57581475[(2S)-2-Methyl-1-piperazinyl]phenylmethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-butyl 4-benzoyl-3-methylpiperazine-1-carboxylate (8.16 g, 26.8 mmol) was dissolved in dichloromethane (200 mL). Trifluoroacetic acid (20.7 ml) was added and the reaction was stirred at rt for 1.5 hours. The reaction was quenched into saturated K2CO3 (30 mL) and neutralized by the portion-wise addition of solid NaHCO3. The layers were separated and extracted twice with dichloromethane. The combined organics were dried (MgSO4) and evaporated to give a yellow oil. MS (M+H)+=205.3.

Workup

  1. customThe reaction was quenched into saturated K2CO3 (30 mL)
  2. additionneutralized by the portion-wise addition of solid NaHCO3
  3. customThe layers were separated
  4. extractionextracted twice with dichloromethane
  5. dry with materialThe combined organics were dried (MgSO4)
  6. customevaporated
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-cb30c2f8c58b427298c22302d42b8756
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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