Hexahydro-1,4-diazepine → HCID 18667856, compound

HRID 1060205Notes

Reaction equation

HRID 1060205 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:8][C:9]1[O:15]C(C)(C)[O:13][C:11](=O)[CH:10]=1>C1(C)C(C)=CC=CC=1>[C:11]([N:1]1[CH2:7][CH2:6][CH2:5][N:4]([C:11](=[O:13])[CH2:10][C:9]([CH3:8])=[O:15])[CH2:3][CH2:2]1)(=[O:13])[CH2:10][C:9]([CH3:8])=[O:15]

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 1

HCID 18667856HCID 18667856, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
124 °C

Procedure

To 1,4-diazacycloheptane (81.90 g, 0.819 mol) in xylene (525 ml) at 122° C. was added with stirring 2,2,6-trimethyl-1,3-dioxen-4-one (232.49 g, 1.637 mol) in xylene (525 ml) over 10 minutes, during which the temperature decreased to 99° C. After heating to 124° C. over 5 minutes vigorous effervescence commenced, and after heating to 127° C. over 5 minutes distillation of acetone (through a Vigreux column) also commenced. Pot temperature was increased to 140° C. over a further 30 minutes, with collection of acetone distillate. After cooling to 15° C. overnight, supernatant liquid was separated from deposited syrup, which was dissolved in dichloromethane. Removal of solvent from combined solutions and drying (91° C./100 Pa) gave N,N′-bis(acetoacetyl)-1,4-diazacycloheptane (BAADCH) as a viscous syrup (211.16 g, 96%), identified by 1H-NMR, 13C-NMR, FT-IR and Raman spectra.

Workup

  1. customdecreased to 99° C
  2. temperatureafter heating to 127° C. over 5 minutes
  3. distillationdistillation of acetone (through a Vigreux column)
  4. temperaturePot temperature was increased to 140° C. over a further 30 minutes, with collection of acetone distillate
  5. temperatureAfter cooling to 15° C. overnight
  6. customsupernatant liquid was separated from deposited syrup, which
  7. dissolutionwas dissolved in dichloromethane
  8. customRemoval of solvent from combined solutions
  9. customdrying (91° C./100 Pa)

Sources & evidence

ORD record
ord-df3467dd95c8435fbbc0102611040f10
Source dataset
uspto-grants-2003_02
Patent number
US06521716B1

Reaction notes

Loading…