Triethylamine → 1-(5,6-Dichloro-3-oxoindan-1-carbonyl)-4-methyl-2-(pyrrolidin-1-ylmethyl)piperazine dihydrochloride

HRID 1493147ノート

反応式

HRID 1493147 の反応式
[ClH:1].Cl.Cl.[CH3:4][N:5]1[CH2:10][CH2:9][NH:8][CH:7]([CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:6]1.C(N(CC)CC)C.[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][C:33]=1[Cl:34])[CH:30]([C:35](Cl)=[O:36])[CH2:29][C:28]2=[O:38].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[ClH:24].[ClH:1].[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][C:33]=1[Cl:34])[CH:30]([C:35]([N:8]1[CH2:9][CH2:10][N:5]([CH3:4])[CH2:6][CH:7]1[CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:36])[CH2:29][C:28]2=[O:38]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 151324075,6-Dichloro-3-oxoindan-1-carbonyl chlorideHCID 189151091-Methyl-3-(pyrrolidin-1-ylmethyl)piperazine trihydrochloride

生成物 1

HCID 189151581-(5,6-Dichloro-3-oxoindan-1-carbonyl)-4-methyl-2-(pyrrolidin-1-ylmethyl)piperazine dihydrochloride収率 91.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 2.0 g of 4-methyl-2-(pyrrolidin-1-ylmethyl)piperazine trihydrochloride in 150 ml of methylene chloride was added 4.3 ml of triethylamine with vigorous stirring in an atmosphere of nitrogen. After stirring for 20 minutes, the mixture was cooled to -10° C. in an ice and salt bath and 50 ml of methylene chloride solution containing 1.9 g of 5,6-dichloro-3-oxoindan-1-carbonyl chloride was added dropwise to it. The reaction mixture was stirred at -10° C. for an hour and a half and subsequently at room temperature for two hours and a half and poured into a saturated aqueous solution of sodium bicarbonate. The resulting aqueous mixture was extracted with diethyl ether and the extract was washed with a saturated aqueous solution of sodium chloride followed by drying over anhydrous magnesium sulfate and distilling off the solvent. The residue was purified by column chromatography through silica gel and 1.60 g of the desired compound was obtained from the fractions eluted with a 10:3 mixture of ethyl acetate and triethylamine. To a solution of the product dissolved in methylene chloride was added a two molar quantity of a 4 N 1,4-dioxane solution of hydrogen chloride and the mixture was concentrated. The residue was recrystallized from a mixture of ethanol and acetone to afford the title compound melting at 250°-255° C. (dec.).

後処理

  1. stirringAfter stirring for 20 minutes
  2. additionwas added dropwise to it
  3. stirringThe reaction mixture was stirred at -10° C. for an hour
  4. extractionThe resulting aqueous mixture was extracted with diethyl ether
  5. washthe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationdistilling off the solvent
  8. customThe residue was purified by column chromatography through silica gel

出典と根拠

ORDレコード
ord-59c50bf8086c4604b34c7e322ada34dd
出典データセット
uspto-grants-1991_06
特許番号
US05021413

反応ノート

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