Methylamine → N-methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine

HRID 646877Notes

Reaction equation

HRID 646877 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1.[CH3:17][NH2:18]>CO>[CH3:17][NH:18][C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 532567081-(5-Fluoro-2-nitrophenyl)piperidine

Product 1

HCID 68680582N-methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(5-fluoro-2-nitro-phenyl)-piperidine (200 mg, 0.890 mmol) in 4 mL of 2M methylamine in MeOH was heated in a sealed tube for 12 h at 80° C. Removal of the solvent under vacuum afforded methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine (209 mg, 100%). Mass spectrum (ESI, m/z): Calcd. for C12H17N3O2, 236.1 (M+H), found 236.1.

Workup

  1. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-fa7d89403fa94764a4872956a4e4a730
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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