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

HRID 1858547노트

반응식

HRID 1858547 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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 3N 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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-70028f097cf740e79f887b1e40967d75
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150526

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