Potassium Carbonate → HCID 59441946, compound

HRID 1014352Notes

Reaction equation

HRID 1014352 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH3:13][N:14]1[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[CH3:13][N:14]1[CH2:20][CH2:19][CH2:18][N:17]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2283491-MethylhomopiperazineHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 59441946HCID 59441946, compoundYield 114%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-fluoro-2-(methyloxy)-1-nitrobenzene (1.0 g, 5.85 mmol) in 15 mL of DMSO was added 1-methylhexahydro-1H-1,4-diazepine (0.8 mL, 6.42 mmol) and potassium carbonate (2.4 g, 17.4 mmol). The reaction mixture was heated at 80° C. for 16 h at which time the reaction was diluted with ethyl acetate and washed with a saturated solution of sodium bicarbonate, water and a saturated sodium chloride solution, dried over Na2SO4 and filtered. Solvents were removed under reduced pressure to give 1-methyl-4-[3-(methyloxy)-4-nitrophenyl]hexahydro-1H-1,4-diazepine (1.77 g, 6.67 mmol) as a yellow solid containing residual DMSO. ESIMS (M+H)+=266

Workup

  1. washwashed with a saturated solution of sodium bicarbonate, water
  2. dry with materiala saturated sodium chloride solution, dried over Na2SO4
  3. filtrationfiltered
  4. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-7879567db82f429f805efbde60a53a03
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…