Sodium Iodide → 1-Ethyl-3,3,5-trimethyl-7-[3-(2-phenylpiperidin-1-yl)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione hydrochloride

HRID 69054

反応式

HRID 69054 の反応式
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[C:9]1([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][NH:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:43]=[CH:42][C:29]2[N:30]([CH2:40][CH3:41])[C:31](=[O:39])[C:32]([CH3:38])([CH3:37])[C:33](=[O:36])[N:34]([CH3:35])[C:28]=2[CH:27]=1.C(OC(=O)C)C.Cl>C(OCC)(=O)C.O.CN(C=O)C>[ClH:21].[CH2:40]([N:30]1[C:31](=[O:39])[C:32]([CH3:37])([CH3:38])[C:33](=[O:36])[N:34]([CH3:35])[C:28]2[CH:27]=[C:26]([O:25][CH2:24][CH2:23][CH2:22][N:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH:15]3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:43]=[CH:42][C:29]1=2)[CH3:41]

参加物

9

反応物 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1030202-PhenylpiperidineHCID 21866389Hydrogen chloride-ethyl acetateHCID 686732537-(3-Chloropropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

生成物 1

HCID 669612001-Ethyl-3,3,5-trimethyl-7-[3-(2-phenylpiperidin-1-yl)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione hydrochloride収率 27.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

Potassium carbonate (0.54 g), sodium iodide (0.21 g), and 2-phenyl piperidine (0.23 g) were added to a DMF solution (15 ml) of 7-(3-chloropropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.44 g). The mixture was stirred at 70° C. for 5 hours. The reaction mixture was cooled to room temperature. Water was added thereto, followed by extraction by ethyl acetate. The organic layer was washed with water and then with saturated saline, and dried with anhydrous magnesium sulfate. After condensation under reduced pressure, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1). The purified product was condensed under reduced pressure. A 4N-Hydrogen chloride ethyl acetate solution (0.2 ml) was added to an ethyl acetate solution (10 ml) of the residue, which was stirred at room temperature. The liquid was condensed to dryness under reduced pressure to give the title compound (0.18 g) as a white amorphous solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction by ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwith saturated saline, and dried with anhydrous magnesium sulfate
  5. customAfter condensation under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1)
  7. customcondensed under reduced pressure
  8. stirringwas stirred at room temperature
  9. customcondensed to dryness under reduced pressure

出典と根拠

ORDレコード
ord-2596dfbb3adc47489b70a46d9f61cf27
出典データセット
uspto-grants-2014_09
特許番号
US08822453B2

関連ノート

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