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

HRID 1356713

반응식

HRID 1356713 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 12084268N,N-dimethyl-N-geranyloxycarbonylmethyl-N-(3-(acetylamino)propyl)ammonium chloride수율 83.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-237901d455644debb59fba2d72264f38
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586639B2

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