4-Chloroaniline → 1-Benzyl-4-((4-chlorophenyl)amino)piperidine-4-carbonitrile

HRID 242571노트

반응식

HRID 242571 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.C[Si]([C:27]#[N:28])(C)C.[OH-].[NH4+]>C(O)(=O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)([C:27]#[N:28])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 78124-ChloroanilineHCID 14923Ammonium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 82115Trimethylsilyl cyanide

생성물 1

HCID 704181-Benzyl-4-((4-chlorophenyl)amino)piperidine-4-carbonitrile수율 81%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

To a solution of 1-Benzyl-piperidin-4-one (2.68 g, 14.20 mmol) in acetic acid (13 ml, glacial) was added 4-Chloro-phenylamine (1.99 g, 15.6 mmol). The reaction was cooled in a cool temperature water bath. Trimethylsilylcyanide (1.89 ml, 14.20 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature and stir overnight under N2. The reaction was cooled to 0° C. Concentrated ammonium hydroxide (15 ml) was added slowly. Next added was cold water. The pH of the mixture was ≈10. The mixture was extracted three times with methylene chloride, and the organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Ether was added to the residue, and the white solid was filtered off and dried under high vacuum to give the titled compound (3.73 g, 81%)

후처리

  1. temperatureThe reaction was cooled in a cool temperature water bath
  2. temperatureThe reaction was cooled to 0° C
  3. additionNext added
  4. extractionThe mixture was extracted three times with methylene chloride
  5. dry with materialthe organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionEther was added to the residue
  9. filtrationthe white solid was filtered off
  10. customdried under high vacuum

출처 및 근거

ORD 기록
ord-373eea7754b64e5e88216d3505296964
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653096B2

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