Potassium Carbonate → Hexahydro-1-(3-methyl-4-nitrophenyl)-1H-1,4-diazepine

HRID 1294399Notes

Reaction equation

HRID 1294399 reaction equation
F[C:2]1[CH:7]=C[CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[C:17]([N:20]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)(=O)[CH3:18]>O>[CH3:5][C:4]1[CH:18]=[C:17]([N:20]2[CH2:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:7]=[CH:2][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 4186202N-Acetylhomopiperazine

Product 1

HCID 13007953Hexahydro-1-(3-methyl-4-nitrophenyl)-1H-1,4-diazepineYield 53.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Fluoronitrobenzene (9.1 g, 0.0586 mol) is dissolved in water (50 ml) and then potassium carbonate (9.7 9, 0.0703 mol) and 1-acetyl-[1,4]diazepane (10 g, 0.0703 mol) are added. The medium is heated at 95° C. for 6 hours, and an orange-coloured solution is obtained. The medium is then cooled to room temperature, and an orange-coloured sticky paste then appears. The maximum amount of water is removed from the reaction medium. Isopropanol is then added to the paste until a yellow solid precipitates. The medium is filtered and, after drying in a vacuum oven at 45° C., a yellow powder is obtained which corresponds to 1-(3-methyl-4-nitrophenyl)-[1,4]diazepane (1). (8.7 g; Yield=53.6%)

Workup

  1. customan orange-coloured solution is obtained
  2. temperatureThe medium is then cooled to room temperature
  3. customThe maximum amount of water is removed from the reaction medium
  4. additionIsopropanol is then added to the paste until a yellow solid
  5. customprecipitates
  6. filtrationThe medium is filtered
  7. customafter drying in a vacuum oven at 45° C.

Sources & evidence

ORD record
ord-4e180161d1a043528d320aa611ce7a1a
Source dataset
uspto-grants-2007_07
Patent number
US07241317B2

Reaction notes

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