Diethyl Ether → N,N-dimethyl-N-geranyloxycarbonylmethyl-N-(3-(dodecanoylamino)propyl)ammonium chloride
Reaction equation
[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]/[CH:32]=[C:33](/[CH2:35][CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])\[CH3:34])=[O:29].ClCC([O-])=O>CCCCCC>[Cl-:26].[CH3:20][N+:18]([CH3:19])([CH2:27][C:28]([O:30][CH2:31]/[CH:32]=[C:33](/[CH2:35][CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])\[CH3:34])=[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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A 22.76 g (0.080 mol) portion of N-dodecanoyl-N′,N′-dimethyl-1,3-diaminopropane and 120 ml of diethyl ether were put into a flask, and 18.46 g (0.080 mol) of geranyl chloroacetate was added thereto at 25° C. spending 5 minutes. The reaction mixture was 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 (3) hereinafter) was obtained as a light yellow viscous oil. Yield 38.50 g (0.0747 mol; yield 93.4%).
Workup
- temperaturecooled
- stirringvigorously stirred
- waitspending 10 minutes
- customprecipitation of the product as a white solid
Sources & evidence
- ORD record
- ord-abc7217f12464149984a59915e60d1ee
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06486333B1
Reaction notes
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