Acetic Anhydride → N-Methyl-N-(4-nitro-3-piperidin-1-yl-phenyl)-acetamide

HRID 32911ノート

反応式

HRID 32911 の反応式
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:4]=1.C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:4]=1)[C:25](=[O:27])[CH3:26]

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68680582N-methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine

生成物 1

HCID 69310207N-Methyl-N-(4-nitro-3-piperidin-1-yl-phenyl)-acetamide収率 71%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine (80 mg, 0.34 mmol, as prepared in the previous step) and triethylamine (118 μL, 0.850 mmol)) in 4 mL of CH2Cl2 was added acetic anhydride (320 μL, 3.40 mmol) via microsyringe and the reaction was allowed to stir overnight. At this time it was diluted with CHCl3 (50 mL), washed with satd aq NaHCO3 (2×50 mL), and dried (Na2SO4). Concentration of the solvent in vacuo and purification of the crude material using preparative TLC (4% MeOH—CHCl3) afforded 67 mg (71%) of the title compound as an oil. Mass spectrum (ESI, m/z): Calcd. for C14H19N3O3, 278.1 (M+H), found 278.1.

後処理

  1. washwashed with satd aq NaHCO3 (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. customConcentration of the solvent in vacuo and purification of the crude material

出典と根拠

ORDレコード
ord-985e2538ee694e8dbb63e0299cab5fff
出典データセット
uspto-grants-2008_09
特許番号
US07427683B2

反応ノート

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