Sodium hydride → HCID 23081564, 화합물

HRID 856040노트

반응식

HRID 856040 반응식
[H-].[Na+].[O:3]=[C:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C=O)C>[O:3]=[C:4]1[N:9]([CH2:23][C:22]2[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:27])[F:28])=[CH:26][CH:25]=2)[CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 123096p-Trifluoromethylbenzyl chlorideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

생성물 1

HCID 23081564HCID 23081564, 화합물수율 91.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (840 mg, 24.5 mmol) was gradually added to a solution of tert-butyl 3-oxopiperazine-1-carboxylate (4.1 g, 20.4 mmol) in DMF (30 ml) while cooling in an ice-bath, and the mixture was stirred at room temperature for 30 minutes. A solution of 4-trifluoromethylbenzyl chloride (5 g, 20.9 mmol) in DMF (5 ml) was added dropwise to the mixture while cooling in an ice-bath, which was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate twice. The extract was washed with water twice and brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride) to afford tert-butyl 3-oxo-4-(4-trifluoromethylbenzyl)piperazine-1-carboxylate (6.7 g, yield 91%) as a colorless crystalline powder.

후처리

  1. temperaturewhile cooling in an ice-bath
  2. temperaturewhile cooling in an ice-bath
  3. stirringwhich was stirred at room temperature for 2 hours
  4. extractionextracted with ethyl acetate twice
  5. washThe extract was washed with water twice
  6. dry with materialbrine, and dried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (methylene chloride)

출처 및 근거

ORD 기록
ord-2a15bf37bbc44482ac02d6817e34bde8
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

반응 노트

불러오는 중…