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

HRID 1992705Notes

Reaction equation

HRID 1992705 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-48b7cda3b92243ef9d21d03910c3a1b5
Source dataset
uspto-grants-2010_01
Patent number
US07649092B2

Reaction notes

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