Sodium hydride → Tert-butyl 4-[(1-benzylpiperidin-3-yl)methyl]-3-oxopiperazine-1-carboxylate

HRID 603180노트

반응식

HRID 603180 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CC1C=CC(S(O[CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][N:31]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:30]2)(=O)=O)=CC=1>CN(C)C=O>[CH2:35]([N:31]1[CH2:32][CH2:33][CH2:34][CH:29]([CH2:28][N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]2=[O:14])[CH2:30]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydride3회HCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 57656889(1-Benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonate

생성물 1

HCID 57656824Tert-butyl 4-[(1-benzylpiperidin-3-yl)methyl]-3-oxopiperazine-1-carboxylate수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of tert-butyl-3-oxopiperazine-1-carboxylate (250 mg) in dimethylformamide (10 mL) was added sodium hydride (55 mg) at room temperature under argon. The mixture was stirred at room temperature 15 minutes before a solution of (1-benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonate (492 mg) in dimethylformamide (5 mL) was added. The mixture was stirred overnight at room temperature before sodium hydride (60 mg) was added and the mixture was stirred for 48 hours. A further quantity of sodium hydride (60 mg) was added and the mixture was stirred for 5 hours and then quenched by the addition of water. The mixture was then partitioned between water and ethyl acetate. The layers were separated and the organic layer washed twice with water and once with brine. The organic layer was then dried over sodium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 70% ethyl acetate in hexane to give the title compound as a colourless oil (95 mg, 20%).

후처리

  1. additionwas added
  2. additionwas added
  3. stirringthe mixture was stirred for 5 hours
  4. customquenched by the addition of water
  5. customThe mixture was then partitioned between water and ethyl acetate
  6. customThe layers were separated
  7. washthe organic layer washed twice with water and once with brine
  8. dry with materialThe organic layer was then dried over sodium sulfate
  9. customevaporated
  10. customThe residue was purified by silica column chromatography
  11. washeluting with a gradient of 0 to 70% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-58bcac76c8e14fb88b034749188408d9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906645B2

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