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1,3-Dibromopropane → 7-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 2177107
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HRID 2177107 반응식
[NH2:1][CH:2]1[CH:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[CH:9]=[C:8]([C:19]#[N:20])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.Br[CH2:22][CH2:23][CH2:24]Br.C(N(CC)CC)C>C(#N)C>[N:1]1([CH:2]2[CH:11]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:10]3[CH:9]=[C:8]([C:19]#[N:20])[CH:7]=[CH:6][C:5]=3[CH2:4][CH2:3]2)[CH2:24][CH2:23][CH2:22]1
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참가 물질

5

반응물 3

HCID 80011,3-DibromopropaneHCID 8471TriethylamineHCID 57471403HCID 57471403, 화합물

생성물 1

HCID 574714047-(Azetidin-1-yl)-8-benzyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
120 °C

실험 절차

7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (790 mg, 3.03 mmol), 1,3-dibromopropane (0.4 mL, 3.93 mmol) and triethylamine (0.914 mL, 6.56 mmol) were dissolved in acetonitrile (8 mL) and the reaction mixture heated to 120° C. in the microwave for 2 h. The solvent was evaporated in vacuo. Water (30 mL) and ethyl acetate (40 mL) were added. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and the solvent evaporated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). Yield: 346 mg (1.14 mmol, 37.6%).

후처리

  1. customThe solvent was evaporated in vacuo
  2. additionWater (30 mL) and ethyl acetate (40 mL) were added
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)

출처 및 근거

ORD 기록
ord-e778b8d694c44758a9d2ec1760d6c59d
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067871B2

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