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

HRID 2170853ノート

反応式

HRID 2170853 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-36bcb924382c4a8db4d73e601405ff10
出典データセット
uspto-grants-2015_06
特許番号
US09051296B2

反応ノート

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