Water → 2-[N-(3-aminopropyl)-N-propylamino]pyridine

HRID 464344노트

반응식

HRID 464344 반응식
[H-].[Na+].[NH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[CH2:14](I)[CH2:15][CH3:16].O>CS(C)=O>[NH2:3][CH2:4][CH2:5][CH2:6][N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH2:14][CH2:15][CH3:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 10606924N-(3-aminopropyl)pyridin-2-amine

생성물 1

HCID 201866052-[N-(3-aminopropyl)-N-propylamino]pyridine수율 40.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매3회

반응 조건

온도
22.5 °C

실험 절차

Sodium hydride (1.14 g) was dissolved in DMSO (20 ml) at 70°-75° C. The solution was cooled and 2-(3-aminopropylamino)pyridine (6.57 g) in DMSO (20 ml) added at room temperature. n-Propyl iodide (8.13 g) in DMSO (10 ml) was added dropwise maintaining the temperature at 20-25° C. After standing overnight, water (250 ml) was added and the mixture extracted with ether. The ether extracts were washed with 2N hydrochloric acid and the aqueous layers basified to pH 10.5. After extracting with ether and chloroform the pH was raised to 14 and again extracted with ether. After drying (K2CO3), the final ether extract, on stripping, afforded 2-[N-(3-aminopropyl)-N-propylamino]pyridine (3.4 g) as an oil which was used without further purification. (ii) 2-[N-(3-aminopropyl)-N-propylamino]pyridine (1.74 g) and 2-methylthio-5-(4-chlorobenzyl)pyrimid-4-one (1.6 g) were fused together on an oil bath at 160° C. for 2 hr. On cooling the residue was crystallised three times from ethanol to give 2-[3(N-propyl-N-pyrid-2-ylamino)propylamino]-5-(4-chlorobenzyl)pyrimid-4-one 1.1H2O, 0.8 g (31%) mp 120°-28° C. (softens).

후처리

  1. temperatureThe solution was cooled
  2. extractionthe mixture extracted with ether
  3. washThe ether extracts were washed with 2N hydrochloric acid
  4. extractionAfter extracting with ether and chloroform the pH
  5. temperaturewas raised to 14
  6. extractionagain extracted with ether
  7. dry with materialAfter drying (K2CO3)
  8. extractionthe final ether extract, on stripping

출처 및 근거

ORD 기록
ord-8719c040087843c2a90b4f8051e4b90c
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04547506

반응 노트

불러오는 중…