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

HRID 1350395

반응식

HRID 1350395 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-add402295cd54915982ffe69bcffa438
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214673B2

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