4-Toluenesulfonyl chloride → 4-Bromo-1-tosylpiperidine

HRID 1616342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616342
[Br:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9]>N1C=CC=CC=1.ClCCl.Cl>[Br:1][CH:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][CH2:3]1

Komponenten

6

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 4209294-Bromopiperidine

Produkt 1

HCID 113590324-Bromo-1-tosylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Bromopiperidine (5.75 g, 23.5 mmol) was dissolved in pyridine (50 mL) and treated with tosyl chloride (5.8 g, 30.5 mmol). The reaction mixture was stirred for 12 h at r.t. and then diluted with dichloromethane (150 mL) and HCl (1 M aqueous solution, 50 mL). The organic layer was washed with brine (80 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (40% EtOAc/hexane) to give 4-bromo-1-tosylpiperidine as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.66 (d, J=8.2 Hz, 2H), 7.34 (d, J=8.2 Hz, 2H), 4.27-4.24 (m, 1H), 3.20-3.17 (m, 2H), 3.13-3.11 (m, 2H), 2.46 (s, 3H), 2.23-2.17 (m, 2H), 2.08-2.05 (m, 2H); MS (ESI) 318.0 (M+H)+.

Aufarbeitung

  1. washThe organic layer was washed with brine (80 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (40% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b18ca18d8e344a2d89ea0b4148b50060
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765788B2

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