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

HRID 32911노트

반응식

HRID 32911 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-985e2538ee694e8dbb63e0299cab5fff
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427683B2

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