Diethyl Ether → N,N-dimethyl-N-(2-phenylethyl)oxycarbonylmethyl-N-(3-(dodecanoylamino)propyl)ammonium chloride

HRID 1356714

Reaktionsgleichung

[C:1]([NH:14][CH2:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(OCC)C.[Cl:26][CH2:27][C:28]([O:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29].ClCC([O-])=O>CCCCCC>[Cl-:26].[CH3:20][N+:18]([CH3:19])([CH2:27][C:28]([O:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29])[CH2:17][CH2:16][CH2:15][NH:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

A 14.22 g (0.050 mol) portion of N-dodecanoyl-N′,N′-dimethyl-1,3-diaminopropane and 120 ml of diethyl ether were put into a flask, and 9.93 g (0.050 mol) of 2-phenylethyl chloroacetate was added thereto at 0 to 5° C. spending 5 minutes. The reaction mixture was further stirred at 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 600 ml of hexane 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 (11) hereinafter) was obtained as a white powder. Yield 20.10 g (0.0416 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-72b9c3c55f7e4d579886fc8d5f0e269d
Quelldatensatz: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06586639B2

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