1-Chloro-3-iodopropane → 3-[N'-(3-Chloropropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium Iodide

HRID 263168

Reaktionsgleichung

Reaktionsgleichung von HRID 263168
[Br-].[CH3:2][N+:3]([CH3:10])([CH3:9])[CH2:4][CH2:5][CH2:6][NH:7][CH3:8].[I:11][CH2:12][CH2:13][CH2:14][Cl:15]>C(#N)C>[I-:11].[Cl:15][CH2:14][CH2:13][CH2:12][N:7]([CH2:6][CH2:5][CH2:4][N+:3]([CH3:10])([CH3:9])[CH3:2])[CH3:8]

Komponenten

4

Edukt 2

HCID 813631-Chloro-3-iodopropaneHCID 21444211N,N,N-Trimethyl-3-(methylamino)propan-1-aminium bromide

Produkt 1

HCID 213163753-[N'-(3-Chloropropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium Iodide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 216.2 mg. (1 mmole) of N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide in 1.5 ml. of acetonitrile is added a solution of 205 mg. (1 mmole) of 3-iodo-1-chloropropane in 0.5 ml. of acetonitrile. The mixture is stirred at room temperature for 2.0 hours and the insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration. The filtrate is evaporated and the solid residue obtained is extracted with methylene chloride. The methylene chloride extract is evaporated to give the oily product which is recrystallized from isopropanol-ether to afford 90 mg. (52%) of product; m.p. 93° (dec.); NMR δ: 2.2 (3H, S, --NCH3); 3.46 (9H, S, --N+Me3).

Aufarbeitung

  1. customthe insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration
  2. customThe filtrate is evaporated
  3. customthe solid residue obtained
  4. extractionis extracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. customis evaporated
  7. customto give the oily product which
  8. customis recrystallized from isopropanol-ether
  9. customto afford 90 mg

Quellen und Nachweise

ORD-Eintrag
ord-ad4325e0b08e4d0881b74275485294cc
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04156693

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