Water → 4-(4-Bromophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)pyridine

HRID 1004981Notes

Reaction equation

HRID 1004981 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 53335251-Benzyl-4-(4-bromophenyl)piperidin-4-ol

Product 1

HCID 112443314-(4-Bromophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 121.6 g (0.35 mol) of 1-benzyl-4-(4-bromo-phenyl)-piperidin-4-ol and 121.6 g of p-toluenesulphonic acid monohydrate (0.64 mol) in 1200 ml of toluene was heated to reflux on a water separator for 4.5 hours. Subsequently, the reaction mixture was cooled to room temperature and adjusted to pH 10 with 3N sodium hydroxide solution. Thereafter, the mixture was extracted firstly with 200 ml and then with 500 ml of methylene chloride. The combined organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and then evaporated under reduced pressure. There were obtained 109.1 g (99% of theory) of 1-benzyl-4-(4-bromo-phenyl)-1,2,3,6-tetrahydro-pyridine as a yellowish solid; MS: 328, 330 (M+H)+.

Workup

  1. temperaturewas heated
  2. extractionThereafter, the mixture was extracted firstly with 200 ml
  3. washThe combined organic phases were washed twice with 100 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7c3b1fdf87d9474c873a3297e9a339ad
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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