Trifluoroacetic acid → HCID 67513198, compound

HRID 1519630Notes

Reaction equation

HRID 1519630 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([S:24][CH3:25])[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:25][S:24][C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:21]=[CH:20][C:19]=1[C:22]#[N:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67517204HCID 67517204, compound

Product 1

HCID 67513198HCID 67513198, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[2-(4-cyano-3-fluorophenyl)ethyl]piperazine-1-carboxylate (440 mg, 1.32 mmol) in 10 mL of DMF was dropped NaSMe (0.66 mL, 1.8 mmol, 21% in water). The mixture was stirred at 70° C. for 3 hours. The reaction was diluted with 40 mL of EtOAc and 40 mL water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to give tert-butyl 4-{2-[4-cyano-3-(methylthio)phenyl]ethyl}piperazine-1-carboxylate (250 mg, 52% yield). MS: m/e 362 (M+1)+. To a solution of tert-butyl4-{2-[4-cyano-3-(methylthio)phenyl]ethyl}piperazine-1-carboxylate (250 mg, 0.69 mmol) in 5 mL of DCM was added 5 mL of TFA was stirred at room temperature for 1 hours, and the reaction was concentrated. The residue was diluted with 30 mL of aq. NaHCO3 and 30 mL of DCM: MeOH (v/v=10/1). The organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated to afford 2-(methylthio)-4-(2-piperazin-1-ylethyl)benzonitrile.

Workup

  1. concentrationthe reaction was concentrated
  2. additionThe residue was diluted with 30 mL of aq. NaHCO3 and 30 mL of DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5f5e39e59efe41c1b8d266020833e6de
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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