Sodium Carbonate → 1-(Diphenylmethyl)-4-[(oxiran-2-yl)methyl]piperazine

HRID 1840729Notes

Reaction equation

HRID 1840729 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:26]([CH:28]1[O:30][CH2:29]1)Br>C(#N)C>[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:26][CH:28]3[O:30][CH2:29]3)[CH2:12][CH2:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 18430EpibromohydrinHCID 70048Benzhydrylpiperazine

Product 1

HCID 102447781-(Diphenylmethyl)-4-[(oxiran-2-yl)methyl]piperazineYield 48.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After 1-(diphenylmethyl)piperazine (10.0 g) was dissolved in acetonitrile (50 ml), sodium carbonate (6.5 g) and epibromohydrin (6.8 g) were added thereto, and the mixture was heated under reflux for 2.5 hours. Salts were separated by filtration, and then the resulting filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Wako gel C-200, 200 g) and eluted with a mixed solvent of 99 parts of chloroform and 1 part of methanol to obtain 1-(diphenylmethyl)-4-(1-(2,3-epoxy)propyl)piperazine (5.9 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. customSalts were separated by filtration
  4. concentrationthe resulting filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (Wako gel C-200, 200 g)
  6. washeluted with a mixed solvent of 99 parts of chloroform and 1 part of methanol

Sources & evidence

ORD record
ord-232967cb37724642af203e768969e785
Source dataset
uspto-grants-2004_01
Patent number
US06683083B1

Reaction notes

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