Potassium Iodide → 1-pyrimidin-2-yl-1,4-diazepane

HRID 1636282Notes

Reaction equation

HRID 1636282 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)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)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

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68163Hexahydro-1,4-diazepineHCID 744042-Chloropyrimidine

Product 1

HCID 27724091-pyrimidin-2-yl-1,4-diazepaneYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

50 ml of acetonitrile was added to 10.0 g (0.1 mole) of homopiperazine, 2.9 g (0.025 mole) of 2-chloropyrimidine, 6.9 g (0.05 mole) of potassium carbonate and a catalytic amount of potassium iodide, and the mixture was refluxed under heating for 11 hours. The mixture was cooled to room temperature and then filtered, the filtrate obtained was concentrated under reduced pressure, and the residue was applied to silica gel column chromatography (eluent; a chloroform:methanol=8:2 mixed solution) to obtain 2.14 g of 1-(2-pyrimidyl)homopiperazine as a pale yellow liquid.

Workup

  1. temperatureunder heating for 11 hours
  2. filtrationfiltered
  3. customthe filtrate obtained
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-dd1f95b2fd884e55b18f349aa1d75c39
Source dataset
uspto-grants-2000_03
Patent number
US06034086

Reaction notes

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