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

HRID 1066997노트

반응식

HRID 1066997 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6fb5428e61214450b5b5ef68a13ac896
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06245773B1

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