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4-Oxobutanoic acid → Ethyl 4-[4-(4-benzyl-piperazin-1-yl)-piperidin-1-yl]-butanoate

HRID 2106515
ノート
印刷プレビュー

反応式

HRID 2106515 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[CH:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25].[C:27](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:28].[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CC(O)=O>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH:14]2[CH2:19][CH2:18][N:17]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:16][CH2:15]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11124-Oxobutanoic acidHCID 11430Potassium CarbonateHCID 36792751-Benzyl-4-piperidin-4-yl-piperazineHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 66941713Ethyl 4-[4-(4-benzyl-piperazin-1-yl)-piperidin-1-yl]-butanoate

試薬・触媒・溶媒 2

HCID 176
Acetic Acid
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Under a nitrogen atmosphere a mixture of 3.11 g (12.0 mmol) 1-benzyl-4-piperidin-4-yl-piperazine and 7.50 mL (12.0 mmol, 15% in water) 4-oxo-butyric acid in 70 mL THF was adjusted to a pH of 5 with AcOH and stirred for 1 h at RT. After cooling to 0° C., 5.35 g (24.0 mmol) sodium triacetoxyborohydride were added batchwise and the reaction mixture was stirred overnight at RT. Within 15 min 80 mL of 30% K2CO3 solution were added dropwise, the aqueous phase was washed twice with EtOAc and evaporated down by half i. vac. 1 M KHSO4 solution was added, the precipitate formed was removed by suction filtering, the filtrate was washed with EtOAc and the aqueous phase was evaporated to dryness i. vac. The residue was taken up in 150 mL ethanolic HCl (1.25 M) and the reaction mixture was stirred overnight at RT. It was evaporated down i. vac., the residue was taken up in a little 15% K2CO3 solution, extracted exhaustively with EtOAc and the combined organic phases were dried over Na2SO4. After elimination of the desiccant and solvent the residue was further reacted without any further purification.

後処理

  1. temperatureAfter cooling to 0° C.
  2. stirringthe reaction mixture was stirred overnight at RT
  3. washthe aqueous phase was washed twice with EtOAc
  4. customevaporated down by half i
  5. addition1 M KHSO4 solution was added
  6. customthe precipitate formed
  7. customwas removed by suction
  8. filtrationfiltering
  9. washthe filtrate was washed with EtOAc
  10. customthe aqueous phase was evaporated to dryness i
  11. stirringthe reaction mixture was stirred overnight at RT
  12. customIt was evaporated down i
  13. extractionextracted exhaustively with EtOAc
  14. dry with materialthe combined organic phases were dried over Na2SO4
  15. customAfter elimination of the desiccant and solvent the residue was further reacted without any further purification

出典と根拠

ORDレコード
ord-121655e4aa1841d39c3aaf368d3f260f
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07579341B2

反応ノート

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