Diisopropylethylamine → Benzo[d]isoxazol-3-yl(4-(4-chlorophenoxy)piperidin-1-yl)methanone

HRID 2170853노트

반응식

HRID 2170853 반응식
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:26]([C:33](Cl)=[O:34])=[N:25]1>ClCCl.C(OCC)(=O)C>[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[C:26]([C:33]([N:10]2[CH2:9][CH2:8][CH:7]([O:6][C:5]3[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:12][CH2:11]2)=[O:34])=[N:25]1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 51998894-(4-Chlorophenoxy)piperidineHCID 10419807Benzo[d]isoxazole-3-carbonyl Chloride

생성물 1

HCID 67168793Benzo[d]isoxazol-3-yl(4-(4-chlorophenoxy)piperidin-1-yl)methanone수율 38.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-(4-chlorophenoxy)piperidine (26 mg, 0.12 mmol), and N,N-diisopropylethylamine (0.086 mL, 0.49 mmol) in dichloromethane (0.5 mL) was added dropwise a solution of benzo[d]isoxazole-3-carbonyl chloride (22 mg, 0.12 mmol) in dichloromethane (0.5 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate (3 mL) and washed with water (1.5 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate) and then preparative LC-MS to give 16.3 mg (37% yield) of the title compound.

후처리

  1. washwashed with water (1.5 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate)

출처 및 근거

ORD 기록
ord-36bcb924382c4a8db4d73e601405ff10
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051296B2

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