Chlorotrimethylsilane → 2-Bromo-1-(4-(piperidin-1-yl)phenyl)ethanone

HRID 18203ノート

反応式

HRID 18203 の反応式
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[Si](C)(C)C.[Br:31]NC(=O)CCC(N)=O>C1COCC1.C(OCC)(=O)C>[Br:31][CH2:14][C:13]([C:10]1[CH:11]=[CH:12][C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:8][CH:9]=1)=[O:15]

参加物

7

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 825614'-PiperidinoacetophenoneHCID 2733832Lithium HexamethyldisilazideHCID 9834204N-Bromosuccinamide

生成物 1

HCID 158645462-Bromo-1-(4-(piperidin-1-yl)phenyl)ethanone

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4′-Piperidinoacetophenone (203 mg, 1.00 mmol) was dissolved in THF (5 mL) and treated with lithium bis(trimethylsilyl)amide (1.10 mL, 11.0M in THF, 1.10 mmol). The solution was stirred for 30 minutes prior to the addition of chlorotrimethylsilane (140 μL, 1.10 mmol). After stirring for an additional 30 minutes N-bromosuccinamide (300 mg, 1.73 mmol) was added and the mixture was refluxed from 4 hours. Standard aqueous/ethyl acetate workup provided a yellow solid which was further purified by silica gel chromatography, eluting with 3:1 hexane/ethyl acetate, to provide 2-bromo-4′-piperidinoacetophenone as an off white solid (209 mg, 74%). 1H NMR (200 MHz, CDCl3) δ 8.75 (d, 2H), 6.84 (d, 2H), 4.61 (s, 2H), 3.40 (m, 4H), 1.68 (m, 6H).

後処理

  1. additionwas added
  2. temperaturethe mixture was refluxed from 4 hours
  3. customwas further purified by silica gel chromatography
  4. washeluting with 3:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-55fbe934d8a74cd6b9e6c6970ad960a3
出典データセット
uspto-grants-2010_06
特許番号
US07741349B2

反応ノート

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