4-Aminomethyltetrahydropyran → N-methyl-N-{3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide

HRID 1987202Notes

Reaction equation

HRID 1987202 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.F[C:10]1[CH:15]=[CH:14][C:13]([N:16]([CH3:20])[C:17](=[O:19])[CH3:18])=[CH:12][C:11]=1[N+:21]([O-:23])=[O:22]>CCO>[CH3:20][N:16]([C:13]1[CH:14]=[CH:15][C:10]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)=[C:11]([N+:21]([O-:23])=[O:22])[CH:12]=1)[C:17](=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 27732104-AminomethyltetrahydropyranHCID 57441080N-(4-fluoro-3-nitrophenyl)-N-methylacetamide

Product 1

HCID 57441081N-methyl-N-{3-nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamideYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Aminomethyltetrahydropyran (10.0 g, 86.5 mmol) was added to a mixture of N-(4-fluoro-3-nitrophenyl)-N-methylacetamide (15.6 g, 73.3 mmol) and TEA (15.3 mL, 11.1 g, 110 mmol) in EtOH (300 mL) at room temperature. The reaction mixture was heated for 6 h at reflux. Upon evaporation of ethanol, the residue was dissolved in EtOAc (400 mL), washed with H2O (3×50 mL), saturated NaCl (3×50 mL), and dried over Na2SO4. After filtration and concentration, 21.7 g (96%) of the title compound was obtained as an orange-red solid. 1H NMR (400 MHz, CHLOROFORM-D): δ 1.38-1.52 (m, 2 H), 1.72-1.81 (m, 2 H), 1.90 (s, 3 H), 1.93-2.02 (m, 1 H), 3.23 (s, 3 H), 3.23-3.27 (m, 2 H), 3.36-3.49 (m, 2 H), 4.01-4.07 (m, 2 H), 6.91 (d, J=9.18 Hz, 1 H), 7.29 (dd, J=9.08, 2.64 Hz, 1 H), 8.05 (d, J=2.34 Hz, 1 H), 8.22 (t, J=5.37 Hz, 1 H). MS (ESI) (M+H)+=309.12.

Workup

  1. temperatureThe reaction mixture was heated for 6 h
  2. temperatureat reflux
  3. customUpon evaporation of ethanol
  4. dissolutionthe residue was dissolved in EtOAc (400 mL)
  5. washwashed with H2O (3×50 mL), saturated NaCl (3×50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-7f9a4919d4cb47ffb69e0e7057a8ca6a
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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