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

HRID 1821087ノート

反応式

HRID 1821087 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-2e3ba6e0ae544488bac4b34d3f5b7733
出典データセット
uspto-grants-2009_10
特許番号
US07605265B2

反応ノート

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