Dimethylamine → Dimethyl carbamic acid 3-[4-(4-methoxy-phenyl)-piperazin-1-yl]-3-oxo-1-phenyl-propyl ester

HRID 44210

反応式

HRID 44210 の反応式
[C:1]([CH2:9][C:10]([O:12]CC)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.[BH4-].[Na+].[CH3:31][NH:32][CH3:33].[O:34]1[CH2:38]CCC1>C1(C)C=CC=CC=1.CO.O>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:10](=[O:12])[CH2:9][CH:1]([O:8][C:38](=[O:34])[N:32]([CH3:33])[CH3:31])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:25][CH2:24]2)=[CH:21][CH:22]=1

参加物

9

反応物 5

HCID 674DimethylamineHCID 7170Ethyl benzoylacetateHCID 8028TetrahydrofuranHCID 2697221-(4-Methoxyphenyl)piperazineHCID 4311764Sodium borohydride

生成物 1

HCID 58387041Dimethyl carbamic acid 3-[4-(4-methoxy-phenyl)-piperazin-1-yl]-3-oxo-1-phenyl-propyl ester

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

Ethyl benzoylacetate (2 mmol) and 4-methoxyphenylpiperazine (2 mmol) were dissolved in toluene, and refluxed for 24 hours. The resulting mixture was concentrated under a reduced pressure to obtain a crude compound, and the crude compound was dissolved in methanol, and cooled to 0° C. Then, sodium borohydride (2 mmol) was added dropwise to the resulting mixture. The mixture was stirred at a room temperature for 2 hours, concentrated under a reduced pressure, diluted with water, and then extracted several times with ethyl acetate to obtain an organic phase. The prepared organic phase was dried over magnesium sulfate, filtered, and then concentrated under a reduced pressure. The resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1) to obtain a compound. The prepared compound was dissolved in tetrahydrofuran (8 mL), and 1,1′-carbodiimidazole (4 mmol) was added to the resulting mixture. Then, the resulting mixture was stirred at a room temperature for 1 hour, and excessive dimethylamine was added to the reaction mixture. The resulting reaction mixture was stirred at a room temperature for 1 hour. The reaction mixture was diluted with water, and extracted several times with ethyl acetate to obtain an organic phase. The prepared organic phase was dried over magnesium sulfate, filtered, and then concentrated under a reduced pressure. The resulting pellet was purified with column chromatography (ethyl acetate) to obtain a title compound.

後処理

  1. temperaturerefluxed for 24 hours
  2. concentrationThe resulting mixture was concentrated under a reduced pressure
  3. customto obtain a crude compound
  4. concentrationconcentrated under a reduced pressure
  5. additiondiluted with water
  6. extractionextracted several times with ethyl acetate
  7. customto obtain an organic phase
  8. dry with materialThe prepared organic phase was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under a reduced pressure
  11. customThe resulting pellet was purified with column chromatography (hexane:ethyl acetate=1:1)
  12. customto obtain a compound
  13. stirringThen, the resulting mixture was stirred at a room temperature for 1 hour
  14. customThe resulting reaction mixture
  15. stirringwas stirred at a room temperature for 1 hour
  16. extractionextracted several times with ethyl acetate
  17. customto obtain an organic phase
  18. dry with materialThe prepared organic phase was dried over magnesium sulfate
  19. filtrationfiltered
  20. concentrationconcentrated under a reduced pressure
  21. customThe resulting pellet was purified with column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-92f844025386451fb2a19e4064e2677d
出典データセット
uspto-grants-2013_09
特許番号
US08541409B2

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