p-Toluenesulfonic acid → 4-(4-Bromophenyl)-1-methanesulfonyl-3,6-dihydro-2H-pyridine

HRID 222572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222572
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 187232054-(4-Bromophenyl)-1-(methanesulphonyl)piperidin-4-ol

Produkt 1

HCID 581111584-(4-Bromophenyl)-1-methanesulfonyl-3,6-dihydro-2H-pyridineAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-(4-bromo-phenyl)-1-methanesulfonyl-piperidin-4-ol (60.00 g, 179.51 mmol) and p-toluenesulfonic acid (9.37 g, 53.85 mmol) in toluene (1.08 L) is stirred at 100° C. for 16 h. The reaction is cooled to 23° C. and successively washed with 2 M aq. sodium hydroxide to pH 10, and water. The phases are separated and the organic layer is dried over anhydrous sodium sulfate, filtered and the solvent is removed. Methyl tert-butyl ether (200 mL) is added and the solid is filtered and washed with methyl tert-butyl ether to obtain 35.0 g of the title compound as a pale brown solid. MS m/e (79Br/81Br) 315, 317 (M+1).

Aufarbeitung

  1. temperatureThe reaction is cooled to 23° C.
  2. washsuccessively washed with 2 M aq. sodium hydroxide to pH 10, and water
  3. customThe phases are separated
  4. dry with materialthe organic layer is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed
  7. additionMethyl tert-butyl ether (200 mL) is added
  8. filtrationthe solid is filtered
  9. washwashed with methyl tert-butyl ether

Quellen und Nachweise

ORD-Eintrag
ord-34568e54a4df4d8aa36f50d7318d88f0
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207344B2

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