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2,6-Diphenylpiperidine → 1-(2,6-Diphenylpiperidin-1-yl)-4-dibenzylamino-2-butene

HRID 486278
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인쇄 미리보기

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HRID 486278 반응식
C(O[CH2:5][CH:6]=[CH:7][CH2:8][N:9]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)C.[C:24]1([CH:30]2[CH2:35][CH2:34][CH2:33][CH:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[NH:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:36]1([CH:32]2[CH2:33][CH2:34][CH2:35][CH:30]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:31]2[CH2:5][CH:6]=[CH:7][CH2:8][N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 130106382,6-DiphenylpiperidineHCID 537897791-Acetoxy-4-dibenzylamino-2-butene

생성물 1

HCID 543268241-(2,6-Diphenylpiperidin-1-yl)-4-dibenzylamino-2-butene

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-acetoxy-4-dibenzylamino-2-butene (3.0 g, 9.8 mmol) and 2,6-diphenylpiperidine (2.3 g, 9.8 mmol) in THF (25 ml) is treated with tetrakis(triphenylphosphine)palladium (0) (0.5 g, 0.45 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo. The residue is redissolved in THF (100 ml) and treated with 20% aqueous sodium hydroxide (25 ml). The mixture is stirred for one hour, concentrated, and extracted with diethyl ether. The ether extracts are dried and concentrated to give an orange oil which is purified by chromatography (silica gel; 5% ethyl acetate in hexanes) to give the title compound in a yield of 2.8 g (59%) as a clear oil. MS m/z 486 (M+)

후처리

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionThe residue is redissolved in THF (100 ml)
  3. additiontreated with 20% aqueous sodium hydroxide (25 ml)
  4. stirringThe mixture is stirred for one hour
  5. concentrationconcentrated
  6. extractionextracted with diethyl ether
  7. dry with materialThe ether extracts are dried
  8. concentrationconcentrated
  9. customto give an orange oil which
  10. customis purified by chromatography (silica gel; 5% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-2c8b5efb00284cbd903ef1994e8acbe6
출처 데이터셋
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05290940

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