Thionyl Chloride → 1-chloro-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane

HRID 1106881Notes

Reaction equation

HRID 1106881 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH2:6][CH2:7][N:8]([CH2:10][CH2:11]O)[CH3:9].S(Cl)([Cl:20])=O>C(Cl)Cl>[Cl:20][CH2:11][CH2:10][N:8]([CH2:7][CH2:6][C:5]1[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 144073182-((3,4-Dimethoxyphenethyl)(methyl)amino)ethanol

Product 1

HCID 136051471-chloro-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol as produced in Example 4-(1) in an amount of 2 g (8.36 mmol) was added to methylene chloride (20 ml) and thionyl chloride (0.91 ml, 12.54 mmol) was slowly added dropwise at room temperature, followed by stirring for 24 h. Thereafter, the reaction mixture was subjected to extraction with methylene chloride and washed with a saturated solution of sodium bicarbonate, followed by drying with anhydrous magnesium sulfate and evaporation of the solvent to yield the end compound 1-chloro-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (2.15 g)

Workup

  1. additionwas slowly added dropwise at room temperature
  2. extractionThereafter, the reaction mixture was subjected to extraction with methylene chloride
  3. washwashed with a saturated solution of sodium bicarbonate
  4. dry with materialby drying with anhydrous magnesium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-0c700e8f71294c2bbba4d65b7ee808af
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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