Diethyl Ether → N,N-dimethyl-N-geranyloxycarbonylmethyl-N-(3-(octanoylamino)propyl) ammonium chloride

HRID 1019316

Reaktionsgleichung

[C:1]([NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(OCC)C.[Cl:22][CH2:23][C:24]([O:26][CH2:27]/[CH:28]=[C:29](/[CH2:31][CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35])\[CH3:30])=[O:25].ClCC([O-])=O>CCCCC>[Cl-:22].[CH3:16][N+:14]([CH3:15])([CH2:23][C:24]([O:26][CH2:27]/[CH:28]=[C:29](/[CH2:31][CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35])\[CH3:30])=[O:25])[CH2:13][CH2:12][CH2:11][NH:10][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 15 °C

Versuchsvorschrift

A 22.84 g (0.100 mol) portion of N-octanoyl-N′,N′-dimethyl-1,3-diaminopropane and 250 ml of diethyl ether were put into a flask, and 24.23 g (0.105 mol) of geranyl chloroacetate was added thereto at 0 to 5° C. spending 10 minutes. The reaction mixture was stirred at 5 to 25° C. for 24 hours, and disappearance of the most part of chloroacetate was confirmed by 1H-NMR. Next, the reaction mixture was slowly added dropwise to 650 ml of pentane which was ice-cooled and vigorously stirred, spending 10 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 (4) hereinafter) was obtained as a light yellow viscous oil. Yield 38.2 g (0.0832 mol; yield 83.2%).

Aufarbeitung

temperaturecooled
stirringvigorously stirred
waitspending 10 minutes
customprecipitation of the product as a white solid

Quellen und Nachweise

ORD-Eintrag: ord-4e235410250c4a59a649f534a832150a
Quelldatensatz: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06486333B1

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