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

HRID 1858547Notes

Reaction equation

HRID 1858547 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-70028f097cf740e79f887b1e40967d75
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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