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

HRID 32911Notes

Reaction equation

HRID 32911 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-985e2538ee694e8dbb63e0299cab5fff
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Reaction notes

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