Trifluoroacetic acid → 4-(3'-Benzylphenyl)-3-(S)-isopropyl-piperazine

HRID 25860

Reaction equation

HRID 25860 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:15]=2)[C@@H:10]([CH:27]([CH3:29])[CH3:28])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC.C([O-])(O)=O.[Na+].[OH-].[Na+]>C(Cl)Cl.C(Cl)Cl.CO.O>[CH2:20]([C:16]1[CH:15]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]2[CH:27]([CH3:29])[CH3:28])[CH:19]=[CH:18][CH:17]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 691298694-(3'-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 207600044-(3'-Benzylphenyl)-3-(S)-isopropyl-piperazineYield 92.92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

275.6 mg (0.70 mmol) 4-(3′-Benzylphenyl)-3-(S)-iso-propyl-piperazine-1-carboxylic acid tert-butyl ester (88) were dissolved in 8 ml dry CH2Cl2 and treated with 8 ml TFA, 0.42 ml H2O and 0.42 ml Et3SiH. The resulting mixture was then stirred at r.t. for 3.5 h before it was poured slowly into sat. aq. NaHCO3-solution. After adding 10% NaOH-solution to the mixture until it became alkaline the solution was extracted with CH2Cl2. The comb. org. fractions were dried over Na2SO4 and evaporated. Column chromatography (CH2Cl2/MeOH (4+1)) yielded 191.1 mg (0.65 mmol, 92.92%) 4-(3′-Benzylphenyl)-3-(S)-isopropyl-piperazine (88a) as an oil.

Workup

  1. extractionwas extracted with CH2Cl2
  2. dry with materialfractions were dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-61b97d2bf9bd41b29d59cda91f201638
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Linked notes

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