Dimethylamine, hydrochloride → 2-(1-Dimethylamino ethyl)pyridine

HRID 1638347

Reaktionsgleichung

Reaktionsgleichung von HRID 1638347
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].Cl.[CH3:11][NH:12][CH3:13].[BH3-]C#N.[Na+].[OH-].[Na+]>CO>[CH3:11][N:12]([CH3:13])[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 10473Dimethylamine, hydrochlorideHCID 142862-AcetylpyridineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 148109872-(1-Dimethylamino ethyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension of g 1.21 (0.01 moles) of 2-acetylpyridine, 1.63 (0.02 moles) of dimethylamine hydrochloride, g 0.63 (0.01 moles) of NaCNBH3 and g 0.4 (0.01 moles) of NaOH in ml.80 of dry methanol was stirred at room temperature for 4 days. The insoluble matter was filtered off and the filtrate was made strongly alkaline with 15% aqueous NaOH. After evaporation of the mathanol, some NaOH pellets were added into the aqueous residue, and the solution was extracted with ether. The combined ethereal solutions were dried on solid NaOH and evaporated i.v. The oily residue (gr 2.8) was chromatographed on 12 g. of silicagel, eluting with CH2Cl2 containing 2% to 10% methanol. 1.7 g. of oily product were obtained, sufficiently pure for the subsequent step.

Aufarbeitung

  1. filtrationThe insoluble matter was filtered off
  2. customAfter evaporation of the mathanol
  3. additionsome NaOH pellets were added into the aqueous residue
  4. extractionthe solution was extracted with ether
  5. dry with materialThe combined ethereal solutions were dried on solid NaOH
  6. customevaporated i.v
  7. customThe oily residue (gr 2.8) was chromatographed on 12 g
  8. washof silicagel, eluting with CH2Cl2 containing 2% to 10% methanol
  9. customof oily product were obtained, sufficiently pure for the subsequent step

Quellen und Nachweise

ORD-Eintrag
ord-8c51d20fbb7948968cb6868f2d6fba9a
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04879300

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