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

HRID 501265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501265
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Step1: 4′-Piperidinoacetophenone (203 mg, 1.00 mmol) was dissolved in THF (5 mL) and treated with lithium bis(trimethylsilyl)amide (1.10 mL, 1.0M 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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f4b93012b5e14a0e80de97e7a1ed7871
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772260B2

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