3-(1,3-Dioxan-2-yl)aniline → HCID 178512007、化合物

HRID 659125ノート

反応式

HRID 659125 の反応式
[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

参加物

7

反応物 3

HCID 6016073-(1,3-Dioxan-2-yl)anilineHCID 16682925TrimethylaluminumHCID 46314739HCID 46314739、化合物

生成物 1

HCID 178512007HCID 178512007、化合物

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒2 回HCID 8900Heptane溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-6f27497884c9483ebcf2bfaaa9559680
出典データセット
uspto-grants-2011_12
特許番号
US08080567B2

反応ノート

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