Potassium Acetate → 3-Chloro-4-[(2-chloroethyl)methylamino]pyridin-2-ylmethyl acetate

HRID 1637620Notes

Reaction equation

HRID 1637620 reaction equation
Cl.[Cl:2][C:3]1[C:4]([CH2:14]Cl)=[N:5][CH:6]=[CH:7][C:8]=1[N:9]([CH2:11][CH2:12][Cl:13])[CH3:10].[C:16]([O-:19])(=[O:18])[CH3:17].[K+]>C(O)(=O)C>[C:16]([O:19][CH2:14][C:4]1[C:3]([Cl:2])=[C:8]([N:9]([CH2:11][CH2:12][Cl:13])[CH3:10])[CH:7]=[CH:6][N:5]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 22117349(3-Chloro-2-chloromethylpyridin-4-yl)-(2-chloroethyl)methylamine hydrochloride

Product 1

HCID 187994093-Chloro-4-[(2-chloroethyl)methylamino]pyridin-2-ylmethyl acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.0 g (10.3 mmol) of (3-chloro-2-chloromethylpyridin-4-yl)-(2-chloroethyl)methylamine hydrochloride and 3.0 g (31 mmol) of potassium acetate are heated at 100° C. for 27 h in 50 ml of glacial acetic acid. The glacial acetic acid is then distilled off and the residue is taken up in 60 ml of ethyl acetate/water (1:1). The mixture is adjusted to pH 8 using sodium bicarbonate solution and extracted with 3×30 ml of ethyl acetate. The organic extracts are washed with water, dried over magnesium sulfate and concentrated. The residue is purified by chromatography on silica gel (eluent: toluenelethyl acetate=1:1). The fractions of Rf =0.25 are concentrated (yield: 1.84 g, 64%) and employed directly for the synthesis of the compound of Example C2.

Workup

  1. distillationThe glacial acetic acid is then distilled off
  2. extractionextracted with 3×30 ml of ethyl acetate
  3. washThe organic extracts are washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography on silica gel (eluent: toluenelethyl acetate=1:1)
  7. concentrationThe fractions of Rf =0.25 are concentrated (yield: 1.84 g, 64%)
  8. customemployed directly for the synthesis of the compound of Example C2

Sources & evidence

ORD record
ord-b269870939b849cdad6164c17624ff5b
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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