2-Chloropropan-1-amine hydrochloride → 5-[2-(Amino)propoxy]methyl-N,N,3-trimethyl-2-furanmethanamine

HRID 1577505

Reaktionsgleichung

Reaktionsgleichung von HRID 1577505
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][OH:11])=[CH:7][C:6]=1[CH3:12])[CH3:3].[CH3:13][C:14]([CH3:17])([O-])C.[K+].Cl.ClC(C)C[NH2:23]>CN(C)C=O>[NH2:23][CH:14]([CH3:17])[CH2:13][O:11][CH2:10][C:8]1[O:9][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[C:6]([CH3:12])[CH:7]=1

Komponenten

5

Edukt 3

HCID 1458552-Chloropropan-1-amine hydrochlorideHCID 205709095-(Dimethylaminomethyl)-4-methyl-2-furanmethanolHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 205709325-[2-(Amino)propoxy]methyl-N,N,3-trimethyl-2-furanmethanamineAusbeute 14,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A mixture of 5-(dimethylaminomethyl)-4-methyl-2-furanmethanol (1.35 g) and potassium tert-butoxide (0.9 g) in dry dimethylformamide (3 ml) at 0° was treated with a solution of 2-chloropropylamine, hydrochloride (0.4 g) in dry dimethylformamide (2 ml). After 20 minutes at ambient temperature, the mixture was quenched with oxalic acid (2 g) and the solvent removed in vacuo. Excess anhydrous sodium carbonate was added and the product extracted into chloroform. The chloroform extract was purified by filtration and the solvent evaporated in vacuo. The residue was purified by column chromatography (silica, methanol: 0.88 ammonia 19:1) affording the title compound (0.1 g).

Aufarbeitung

  1. customthe mixture was quenched with oxalic acid (2 g)
  2. customthe solvent removed in vacuo
  3. additionExcess anhydrous sodium carbonate was added
  4. extractionthe product extracted into chloroform
  5. extractionThe chloroform extract
  6. filtrationwas purified by filtration
  7. customthe solvent evaporated in vacuo
  8. customThe residue was purified by column chromatography (silica, methanol: 0.88 ammonia 19:1)

Quellen und Nachweise

ORD-Eintrag
ord-5dd8b30e58424798919e0bd58e6528fe
Quelldatensatz
uspto-grants-1981_09
Patentnummer
US04288443

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