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

HRID 1493147노트

반응식

HRID 1493147 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-59c50bf8086c4604b34c7e322ada34dd
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05021413

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