3-(1,3-Dioxan-2-yl)aniline → HCID 178512007, 화합물

HRID 659125노트

반응식

HRID 659125 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10].C[Al](C)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][C:20]=1[C:31]#[N:32]>C1(C)C=CC=CC=1.CCCCCCC.C(Cl)Cl.CO>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([NH:10][C:31]([C:20]2[CH:21]=[C:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:23]=[CH:24][C:19]=2[F:18])=[NH:32])[CH:11]=[CH:12][CH:13]=1

참가 물질

7

반응물 3

HCID 6016073-(1,3-Dioxan-2-yl)anilineHCID 16682925TrimethylaluminumHCID 46314739HCID 46314739, 화합물

생성물 1

HCID 178512007HCID 178512007, 화합물

시약·촉매·용매 3

HCID 1140Toluene용매2회HCID 8900Heptane용매HCID 21226129Dichloromethane methanol용매

실험 절차

To 3-(1,3-dioxan-2-yl)aniline (55) (336 mg, 1.87 mmol) in toluene (7.5 mL) cooled to 0° C. was added a 2M trimethylaluminum solution in heptane (1.32 mL) dropwise and the resulting mixture was stirred at ambient temperature for 3.5 hours. The nitrile (54) (370 mg, 1.88 mmol) in toluene (7.5 mL) was added and the reaction heated to 70° C. overnight. The reaction was then cooled, poured onto a slurry of silica in DCM/MeOH and the organics flushed through with further DCM/MeOH. The filtrate was concentrated in vacuo and the residue purified by column chromatography using a gradient of EtOAc in heptane (5-100%) to yield the title compound. Yield: 378 mg, 53%; LC-MS tr 1.32 min; HPLC Purity: 71%; MS (ES+) m/z 377 (M+H)

후처리

  1. temperaturethe reaction heated to 70° C. overnight
  2. temperatureThe reaction was then cooled
  3. customthe organics flushed through with further DCM/MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by column chromatography

출처 및 근거

ORD 기록
ord-6f27497884c9483ebcf2bfaaa9559680
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080567B2

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