Dichloromethane → (S)-1-Benzyl-3-(3-phenyl-allyl)-piperazine

HRID 1350395Notes

Reaction equation

HRID 1350395 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][CH:16]=2)[CH2:10][C@@H:9]1[CH2:21][CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:14]([N:11]1[CH2:12][CH2:13][NH:8][C@@H:9]([CH2:21][CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:10]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 69486789(S)-4-Benzyl-2-(3-phenyl-allyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69486967(S)-1-Benzyl-3-(3-phenyl-allyl)-piperazineYield 82.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolve (S)-4-benzyl-2-(3-phenyl-allyl)-piperazine-1-carboxylic acid tert-butyl ester (2.37 g, 6.04 mmol) in toluene (50 mL) and treat with trifluoroacetic acid (10.3 g, 90.5 mmol) at room temperature, and stir the reaction mixture. After overnight, dilute the reaction with CH2Cl2, and basify with 2N NaOH (50 mL), extract the aqueous solution with CH2Cl2, wash the combined organic layers brine, dry over Na2SO4. Pass the crude product through a SCX column (10 g), collect the 0.2N NH3/MeOH eluent and concentrate to give 1.46 g of the title compound: mass spectrum (Electrospray): m/z=293.3 (M+1). 1H NMR (400 MHz, CDCl3): δ7.35–7.19 (m, 10H), 6.54–6.47 (m, 1H) 6.18–6.11, 5.70–5.60 (m, 1H), 3.70 (s, 2H), 2.97–2.73 (m, 5H), 2.40–2.18 (m, 2H), 2.09–2.00 (m, 1H), 1.83 (t, 1H, J=9.8 Hz).

Workup

  1. additiondilute
  2. extractionextract the aqueous solution with CH2Cl2
  3. washwash the combined organic layers brine
  4. dry with materialdry over Na2SO4
  5. customPass the crude product through a SCX column (10 g), collect the 0.2N NH3/MeOH eluent
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-add402295cd54915982ffe69bcffa438
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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