Water → 1-Benzyl-4-(3-bromophenyl)-1,2,3,6-tetrahydro-pyridine

HRID 1004926ノート

反応式

HRID 1004926 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2(O)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.O.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19](S(O)(=O)=O)=[CH:18][CH:17]=1.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:26]([N:11]1[CH2:12][CH:13]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:9][CH2:10]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 221287224-(3-Bromophenyl)piperidin-4-ol

生成物 1

HCID 221269161-Benzyl-4-(3-bromophenyl)-1,2,3,6-tetrahydro-pyridine収率 36%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 28.2 g (81.4 mmol) of 4-(3-bromophenyl)-piperidin-4-ol in 600 ml of toluene was treated with 30 g (157 mmol) of p-toluenesulphonic acid monohydrate and heated to reflux on a water separator for 4 hours. Subsequently, the reaction mixture was cooled to room temperature and adjusted to pH 10 with 3 N sodium hydroxide solution. Thereafter, it was firstly extracted three times with 500 ml of methylene chloride. The combined organic phases were washed three times with 200 ml of water each time, dried over magnesium sulphate and then evaporated under reduced pressure. The crude product was purified by chromatography on silica gel with a 1:1 mixture of methylene chloride and hexane as the eluent. There were obtained 9.5 g (36% of theory) of 1-benzyl-4-(3-bromophenyl)-1,2,3,6-tetrahydro-pyridine as a light yellow oil; MS: 327, 329 (M+H)+.

後処理

  1. temperatureheated
  2. extractionThereafter, it was firstly extracted three times with 500 ml of methylene chloride
  3. washThe combined organic phases were washed three times with 200 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by chromatography on silica gel with a 1:1 mixture of methylene chloride and hexane as the eluent

出典と根拠

ORDレコード
ord-703e04524a90427e96a1d2a64765b36d
出典データセット
uspto-grants-2000_04
特許番号
US06051712

反応ノート

読み込み中…