Ethyl Acetate → 1-Acetyl-4-[3-(piperidin-1-yl)phenylamino]-piperidine dihydrochloride

HRID 1079399노트

반응식

HRID 1079399 반응식
[ClH:1].Cl.[NH2:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[C:16]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)(=[O:18])[CH3:17].C([BH3-])#N.[Na+].C(OCC)(=O)C>CO.O>[ClH:1].[ClH:1].[C:16]([N:19]1[CH2:24][CH2:23][CH:22]([NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[CH:5]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 122563N-Acetyl-4-piperidoneHCID 5003444Sodium cyanoborohydrideHCID 233669441-(3-Aminophenyl)piperidine dihydrochloride

생성물 1

HCID 233669001-Acetyl-4-[3-(piperidin-1-yl)phenylamino]-piperidine dihydrochloride수율 132.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of N-(3-aminophenyl)piperidine dihydrochloride (3.73 g) and 1-acetyl-4-piperidone (2.1 g) in methanol (30 ml) was added sodium cyano borohydride (1.9 g), followed by stirring at room temperature for 5 hours. To the mixture were added ethyl acetate ester (20 ml) and water (30 ml), the organic layer was dried over anhydrous sodium sulfate and then the solvent was distilled off. The residual oily compound was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate ester). The oily compound was dissolved in dioxane (10 ml) and to the mixture was added 6N solution of hydrogen chloride in dioxane (2 ml). Then, the solvent was removed to obtain a colorless amorphous solid (3.7 g).

후처리

  1. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  2. distillationthe solvent was distilled off
  3. customThe residual oily compound was separated
  4. custompurified by silica gel column chromatography (developing solvent: ethyl acetate ester)
  5. dissolutionThe oily compound was dissolved in dioxane (10 ml) and to the mixture
  6. additionwas added 6N solution of hydrogen chloride in dioxane (2 ml)
  7. customThen, the solvent was removed

출처 및 근거

ORD 기록
ord-3f0c13b8f65045b798b39ce173b37ba1
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05580883

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