Trifluoroacetic acid → 2-amino-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

HRID 11686

Reaction equation

HRID 11686 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([N:11]1[CH2:16][C@H:15]([CH3:17])[N:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH2:13][C@H:12]1[CH3:26])=[O:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH2:8][C:9]([N:11]1[CH2:16][C@H:15]([CH3:17])[N:14]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH2:13][C@H:12]1[CH3:26])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69655545{2-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethyl}-carbamic Acid tert-butyl Ester

Product 1

HCID 696557642-amino-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanoneYield 112.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of {2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (1.45 g, 3.28 mmol) in dichloromethane (38 mL) was added trifluoroacetic acid (20 mL). The reaction was stirred at ambient temperature for two hours. The reaction was diluted with dichloromethane and washed with 1N sodium hydroxide. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated to the give the title compound (1.03 g).

Workup

  1. washwashed with 1N sodium hydroxide
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to the

Sources & evidence

ORD record
ord-a298c342cfc74e5f87a5ae2028897c0b
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

Loading…