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

HRID 1619215Notes

Reaction equation

HRID 1619215 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:9]1[N:14]=[CH:13][CH:12]=[CH:11][N:10]=1>C(O)C>[N:10]1[CH:11]=[CH:12][CH:13]=[N:14][C:9]=1[N:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]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 702EthanolSolvent

Procedure

To a solution of homopiperazine (3.5 g, 35 mmol) in ethanol (100 ml) at 40° C., was added portionwise 2-chloropyrimidine (2.0 g, 17.5 mmol). The mixture was stirred for 1 hour then concentrated in vacuo. The residue was dissolved in methylene chloride (75 ml) and washed with a saturated solution of sodium bicarbonate and brine. Layers were separated, and the organic layer was dried over magnesium sulfate and concentrated. The resulting residue was purified by flash chromatography and a semi-solid (1.0 g) was collected and used as is.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride (75 ml)
  3. washwashed with a saturated solution of sodium bicarbonate and brine
  4. customLayers were separated
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography
  8. customa semi-solid (1.0 g) was collected

Sources & evidence

ORD record
ord-28d31164e63f4d848ec51404d881586d
Source dataset
uspto-grants-2014_07
Patent number
US08772291B2

Reaction notes

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