Amides, C5-9, N-(3-(dimethylamino)propyl) → N,N-dimethyl-N-geranyloxycarbonylmethyl-N-(3-(acetylamino)propyl)ammonium chloride

HRID 1019317

Reaktionsgleichung

Reaktionsgleichung von HRID 1019317
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][N:8]([CH3:10])[CH3:9])(=[O:3])[CH3:2].[Cl:11][CH2:12][C:13]([O:15][CH2:16]/[CH:17]=[C:18](/[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])\[CH3:19])=[O:14]>C(OCC)C>[Cl-:11].[CH3:9][N+:8]([CH3:10])([CH2:12][C:13]([O:15][CH2:16]/[CH:17]=[C:18](/[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])\[CH3:19])=[O:14])[CH2:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 349255Amides, C5-9, N-(3-(dimethylamino)propyl)HCID 5890636(E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetate

Produkt 1

HCID 12084268N,N-dimethyl-N-geranyloxycarbonylmethyl-N-(3-(acetylamino)propyl)ammonium chlorideAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A 7.21 g (0.05 mol) portion of N-acetyl-N′,N′-dimethyl-1,3-diaminopropane and 150 ml of diethyl ether were put into a flask, and 11.65 g (0.0505 mol) of geranyl chloroacetate was added thereto at 0 to 5° C. spending 10 minutes. The reaction mixture was stirred for 2 hours while cooling on ice to observe precipitation of the product. This was further stirred at 25° C. for 12 hours, and disappearance of the most part of chloroacetate was confirmed by 1H-NMR. Next, the solvent was evaporated under a reduced pressure, and the reaction mixture as the residual viscous oil was dissolved in 20 ml of dichloromethane and slowly added dropwise to 400 ml of diethyl ether which was ice-cooled and vigorously stirred, spending 5 minutes, to effect precipitation of the product as a white solid. Thereafter, in the same manner as described in Inventive Example 1, the title compound (to be referred to as betaine ester (5) hereinafter) was obtained as a light yellow viscous oil. Yield 15.6 g (41.6 mmol; yield 83.2%).

Aufarbeitung

  1. temperaturewhile cooling on ice
  2. customprecipitation of the product
  3. stirringThis was further stirred at 25° C. for 12 hours
  4. customNext, the solvent was evaporated under a reduced pressure
  5. dissolutionthe reaction mixture as the residual viscous oil was dissolved in 20 ml of dichloromethane
  6. additionslowly added dropwise to 400 ml of diethyl ether which
  7. temperaturecooled
  8. stirringvigorously stirred
  9. waitspending 5 minutes
  10. customprecipitation of the product as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-e12f07472f534f018409cf56a078f4c0
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06486333B1

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