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

HRID 1350395ノート

反応式

HRID 1350395 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-add402295cd54915982ffe69bcffa438
出典データセット
uspto-grants-2007_05
特許番号
US07214673B2

反応ノート

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