Sodium hydride → tert-Butyl 4-cyano-4-(2,4-dichlorophenyl)piperidine-1-carboxylate

HRID 1066997ノート

反応式

HRID 1066997 の反応式
[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:11][CH2:12]Cl)[CH2:8][CH2:9]Cl)([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[CH2:23][C:24]#[N:25].[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:7]1[CH2:11][CH2:12][C:23]([C:24]#[N:25])([C:17]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[Cl:15])[CH2:9][CH2:8]1)=[O:14])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 805662,4-DichlorophenylacetonitrileHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

生成物 1

HCID 49760258tert-Butyl 4-cyano-4-(2,4-dichlorophenyl)piperidine-1-carboxylate収率 45.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To bis(2-chloroethyl)-carbamic acid tert-butyl ester (1.0 g, 3.8 mmol) and 2,4-dichlorophenyl acetonitrile (0.708 g, 3.8 mmol) in DMF (35 ml), NaH (95%) (0.258 g, 9.68 mmol) was added in one batch at 0° C. The solution was stirred for 10 minutes at room temperature. When foaming subsided, the solution was heated at 60° C. for 24 hours. It was then quenched with water at 0° C. and concentrated. The residue was extracted with ethyl acetate (25 mL) and washed three times with water (15 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (hexane:ethyl acetate 4:1) yielded 0.620 g (45%) of the product as a syrup.

後処理

  1. temperaturethe solution was heated at 60° C. for 24 hours
  2. customIt was then quenched with water at 0° C.
  3. concentrationconcentrated
  4. extractionThe residue was extracted with ethyl acetate (25 mL)
  5. washwashed three times with water (15 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography (hexane:ethyl acetate 4:1)

出典と根拠

ORDレコード
ord-6fb5428e61214450b5b5ef68a13ac896
出典データセット
uspto-grants-2001_06
特許番号
US06245773B1

反応ノート

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