Sodium Hydroxide → 4-(Chloro(4-chlorophenyl)methyl)-1-methylpiperidine

HRID 2224117Notes

Reaction equation

HRID 2224117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)O)=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:19][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 541856alpha-[4-Chlorophenyl]-1-methyl-4-piperidinemethanol

Product 1

HCID 597169334-(Chloro(4-chlorophenyl)methyl)-1-methylpiperidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-chlorophenyl 1-methylpiperidin-4-yl methanol 1.2 g (5.02 mmol) in toluene (5 ml) was added thionyl chloride (0.45 ml) dropwise. The resulting mixture was stirred at room temperature over night. The mixture was then made alkaline with NaOH solution and extracted with ethyl acetate (3×40). The combined organic solution was dried and concentrated to give 1.2 g of desired product.

Workup

  1. extractionextracted with ethyl acetate (3×40)
  2. customThe combined organic solution was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9c6b6b31955644ab86a14944f0073c0e
Source dataset
uspto-grants-2008_05
Patent number
US07378420B2

Reaction notes

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