Thionyl Chloride → N-(2-Chloroethyl)-N-methylbenzylamine hydrochloride

HRID 1685151Notes

Reaction equation

HRID 1685151 reaction equation
[CH2:1]([N:8]([CH3:12])[CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O>Cl>[ClH:15].[CH2:1]([N:8]([CH2:9][CH2:10][Cl:15])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66876N-Benzyl-N-methylethanolamine

Product 1

HCID 12822620N-(2-Chloroethyl)-N-methylbenzylamine hydrochlorideYield 133.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Combine hydrogen chloride (50 mL; 4M in dioxane), N-benzyl-N-methylethanolamine (61.12 mmol; 10 g), thionyl chloride (73.30 mmol; 5.34 mL) and heat to 90° C. Stir for 2 h, evaporate and crush the solids under ether, sonicate 15 min, filter, wash with ether, dry under vacuum to provide the title compound (10.75 g; 80%). MS (ES): m/z=184 (M+H).

Workup

  1. customevaporate
  2. customcrush the solids under ether
  3. customsonicate 15 min
  4. filtrationfilter
  5. washwash with ether
  6. customdry under vacuum

Sources & evidence

ORD record
ord-9d38b831c5ad4fc196755f28c7a7ebd9
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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