Methyl iodide → 4-[N-(4-Chloro-benzyl)-methylamino]-cyclohexanol

HRID 569095Notes

Reaction equation

HRID 569095 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][CH:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:17](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]([CH3:17])[CH:8]2[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136706584-(4-Chloro-benzylamino)-cyclohexanol

Product 1

HCID 136706604-[N-(4-Chloro-benzyl)-methylamino]-cyclohexanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.2 g (30 mMol) of 4-[N-(4-chloro-benzyl)-amino]-cyclohexanol are dissolved in 30 ml of dimethyl-formamide, and after the addition of 2.2 g (16 mMol) of potassium carbonate, 4.26 g (30 mMol) of methyliodide are added dropwise. When the slightly exothermic reaction has ended, the mixture is concentrated by evaporation, mixed with water and extracted with chloroform. The concentrated extracts are chromatographed on silica gel to purify them (eluant; methylene chloride/methanol=20/1).

Workup

  1. additionare added dropwise
  2. customWhen the slightly exothermic reaction
  3. concentrationthe mixture is concentrated by evaporation
  4. additionmixed with water
  5. extractionextracted with chloroform
  6. customThe concentrated extracts are chromatographed on silica gel
  7. customto purify them (eluant; methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-cf350ff17b494516829bc7e2dc5d9f47
Source dataset
uspto-grants-1988_03
Patent number
US04731374

Reaction notes

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