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

HRID 556956ノート

反応式

HRID 556956 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-bd3355c65d724d289267b885cae1aa2b
出典データセット
uspto-grants-2011_11
特許番号
US08058287B2

反応ノート

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