Hexahydro-1,4-diazepine → 1-pyrimidin-2-yl-1,4-diazepane

HRID 2376653Notes

Reaction equation

HRID 2376653 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1>CCO>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 744042-Chloropyrimidine

Product 1

HCID 27724091-pyrimidin-2-yl-1,4-diazepane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

An ice bath is used to cool a solution of 3 g of 2-chloropyrimidine in 20 ml of EtOH which is then admixed dropwise with a solution of 13 g of 1,4-diazepane in 50 ml of EtOH, left with stirring in the cold for 30 minutes and then at AT for 24 hours. It is concentrated under vacuum, the residue is taken up with 100 ml of AcOEt and 100 ml of saturated K2CO3 solution, the system is decanted, the organic phase is diluted by adding 100 ml of AcOEt, the organic phase is washed with saturated K2CO3 solution and dried over Na2SO4 and the solvent is evaporated under vacuum. This gives the expected product, which is used as it is.

Workup

  1. customAn ice bath is used
  2. waitleft
  3. waitat AT for 24 hours
  4. concentrationIt is concentrated under vacuum
  5. customthe system is decanted
  6. additionthe organic phase is diluted
  7. additionby adding 100 ml of AcOEt
  8. washthe organic phase is washed with saturated K2CO3 solution
  9. dry with materialdried over Na2SO4
  10. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-bcba9d8cec114a779f4dd6f0b92c6384
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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