Potassium Carbonate → N-[3-(6-methyl-3-pyridyl)acryloyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamine

HRID 868333노트

반응식

HRID 868333 반응식
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(C)(C)C.[C:20]1([CH:26]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][CH2:36][NH2:37])[CH2:29][CH2:28]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(N(CC)CC)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([NH:37][CH2:36][CH2:35][CH2:34][CH2:33][N:30]2[CH2:31][CH2:32][N:27]([CH:26]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:28][CH2:29]2)=[O:12])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 62493Pivaloyl chlorideHCID 139569931-(4-Aminobutyl)-4-(diphenylmethyl)piperazineHCID 541408533-(6-Methyl-3-pyridyl)acrylic acid

생성물 1

HCID 65933N-[3-(6-methyl-3-pyridyl)acryloyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamine수율 72.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매4회HCID 8471Triethylamine용매

반응 조건

온도
-5 °C

실험 절차

To a suspension of 2.71 g of 3-(6-methyl-3-pyridyl)acrylic acid in 70 ml of dry tetrahydrofuran, a solution of 1.68 g of triethylamine in 5 ml of dry tetrahydrofuran is added at room temperature. The resulting solution is cooled to -5° C., and a solution of 2.0 g of pivaloyl chloride in 5 ml of dry tetrahydrofuran is added slowly. The mixture is stirred at the same temperature for 0.5 hour and cooled to -10° C., and a solution of 6.43 g of 4-(4-diphenylmethyl-1-piperazinyl)butylamine in 5 ml of dry tetrahydrofuran is added slowly. The mixture is stirred for 0.5 hour at between -10° C. and -5° C. and then at room temperature overnight. To the reaction mixture is added 50 ml of 10% aqueous potassium carbonate, and the resulting mixture is extracted with three 100-ml portions of ethyl acetate. The combined extracts are washed with water and dried over magnesium sulfate, and the solvent is distilled off. The residue is recrystallized from acetonitrile to give 5.63 g of the title compound, m.p. 129°-131° C.

후처리

  1. temperaturecooled to -10° C.
  2. stirringThe mixture is stirred for 0.5 hour at between -10° C. and -5° C.
  3. customat room temperature
  4. customovernight
  5. extractionthe resulting mixture is extracted with three 100-ml portions of ethyl acetate
  6. washThe combined extracts are washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent is distilled off
  9. customThe residue is recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-a404f031ff374c6fb9af01ee832418c5
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04778796

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