Hydrochloric Acid → 908117-05-5

HRID 873686Notes

Reaction equation

HRID 873686 reaction equation
[Na].[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][OH:6].[NH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11](Cl)[CH:10]=1.Cl.[Cl-].[Na+]>O1CCCC1>[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][O:6][C:11]1[CH:10]=[C:9]([NH2:8])[CH:14]=[CH:13][N:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 79022-(Dimethylamino)ethanolHCID 844322-Chloropyridin-4-amineHCID 5360545Sodium

Product 1

HCID 59244595908117-05-5

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.55 g of sodium and 26.9 mL of 2-dimethylaminoethanol in tetrahydrofuran (180 mL) is heated to reflux for 20 hours. The reaction mixture is cooled to room temperature, treated with 4 g of 4-amino-2-chloropyridine and heated to 140° C. for 20 min (microwave irradiation). The reaction mixture is treated with concentrated HCl to pH 8 at 0° C., saturated with sodium chloride and extracted with diethyl ether. The organics are dried (magnesium sulfate) and concentrated to 11.9 g of crude product which is purified by silica gel chromatography (90:10:1 ethyl acetate/methanol/ammonium hydroxide) to give 2-(2-dimethylamino-ethoxy)-pyridin-4-ylamine as tan crystals. MS (m/z): 182 (M+1); Rf 0.1 (90:10:1 ethyl acetate/methanol/ammonium hydroxide).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 20 hours
  3. temperatureheated to 140° C. for 20 min
  4. custom(microwave irradiation)
  5. extractionextracted with diethyl ether
  6. dry with materialThe organics are dried (magnesium sulfate)
  7. concentrationconcentrated to 11.9 g of crude product which
  8. customis purified by silica gel chromatography (90:10:1 ethyl acetate/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-9841aea82514498e975297f37a0cc5eb
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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