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

HRID 2276660Notes

Reaction equation

HRID 2276660 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-4d2acac9bad94411bd74234445881298
Source dataset
uspto-grants-2015_09
Patent number
US09133073B2

Reaction notes

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