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

HRID 1356712

反応式

HRID 1356712 の反応式
[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]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 89889Caprylamidopropyl dimethylamineHCID 518964ChloroacetateHCID 5890636(E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetate

生成物 1

HCID 12084266N,N-dimethyl-N-geranyloxycarbonylmethyl-N-(3-(octanoylamino)propyl) ammonium chloride収率 83.2%

試薬・触媒・溶媒 1

HCID 8003Pentane溶媒

反応条件

温度
15 °C

実験手順

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%).

後処理

  1. temperaturecooled
  2. stirringvigorously stirred
  3. waitspending 10 minutes
  4. customprecipitation of the product as a white solid

出典と根拠

ORDレコード
ord-3d3003e858794f7d9210f085ade68e68
出典データセット
uspto-grants-2003_07
特許番号
US06586639B2

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