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

HRID 222572노트

반응식

HRID 222572 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 581111584-(4-Bromophenyl)-1-methanesulfonyl-3,6-dihydro-2H-pyridine수율 61.7%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-34568e54a4df4d8aa36f50d7318d88f0
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207344B2

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