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

HRID 222572ノート

反応式

HRID 222572 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-34568e54a4df4d8aa36f50d7318d88f0
出典データセット
uspto-grants-2012_06
特許番号
US08207344B2

反応ノート

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