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

HRID 464344ノート

反応式

HRID 464344 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒3 回

反応条件

温度
22.5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8719c040087843c2a90b4f8051e4b90c
出典データセット
uspto-grants-1985_10
特許番号
US04547506

反応ノート

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