1,3-Propanediamine → N-(3-aminopropyl)-6-chloro-1,2,3,4-tetrahydroacridin-9-amine

HRID 1821087노트

반응식

HRID 1821087 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12](Cl)=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]1)=[N:5]2.[NH2:17][CH2:18][CH2:19][CH2:20][NH2:21].C(O)CCCC.C(=O)(O)[O-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:17][CH2:18][CH2:19][CH2:20][NH2:21])=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]1)=[N:5]2

참가 물질

5

반응물 4

HCID 4281,3-PropanediamineHCID 62761-PentanolHCID 2196646,9-Dichloro-1,2,3,4-tetrahydroacridineHCID 516892Sodium Bicarbonate

생성물 1

HCID 23645224N-(3-aminopropyl)-6-chloro-1,2,3,4-tetrahydroacridin-9-amine수율 87%

실험 절차

To a sealed tube was charged a mixture of 6,9-dichloro-1,2,3,4-tetrahydroacridine (1.0 g, 3.97 mmoL), 1,3-diaminopropane (1.67 mL, 19.83 mmoL) and 4 mL 1-pentanol. The mixture was heated to 160 degree Celsius for 24 h. After cooled down and saturated sodium bicarbonate was added, the mixture was extracted with dichloromethane three times. The combined extract was dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography on silica gel with 10-20% MeOH/CH2Cl2 (1% ammonium hydroxide) to give the desired product as brown oil (1.0 g, 87%).

후처리

  1. additionTo a sealed tube was charged
  2. temperatureThe mixture was heated to 160 degree Celsius for 24 h
  3. temperatureAfter cooled down
  4. extractionthe mixture was extracted with dichloromethane three times
  5. extractionThe combined extract
  6. dry with materialwas dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by column chromatography on silica gel with 10-20% MeOH/CH2Cl2 (1% ammonium hydroxide)

출처 및 근거

ORD 기록
ord-2e3ba6e0ae544488bac4b34d3f5b7733
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605265B2

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