Thionyl Chloride → 2-(N-(2-fluorobenzyl)-N-methylamino)ethyl chloride

HRID 1743666Notes

Reaction equation

HRID 1743666 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4][N:5]([CH2:7][CH2:8]O)[CH3:6].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4][N:5]([CH2:7][CH2:8][Cl:16])[CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 219645192-[(2-Fluoro-benzyl)-methyl-amino]-ethanol

Product 1

HCID 219645502-(N-(2-fluorobenzyl)-N-methylamino)ethyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(N-(2-fluorobenzyl)-N-methylamino)-ethanol (Step B, 7.51 g, 41 mmol) in dry toluene (50 ml) was added thionyl chloride (16 ml). The reaction mixture was stirred at room temperature for 16 hours and concentrated. The crude mixture was diluted with chloroform and washed with aq NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated to provide the title compound which was used without further purification.

Workup

  1. concentrationconcentrated
  2. additionThe crude mixture was diluted with chloroform
  3. washwashed with aq NaHCO3, water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13ad780a3f6d4e55b7f2f2d6f74650e4
Source dataset
uspto-grants-2006_03
Patent number
US07012071B2

Reaction notes

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