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

HRID 1464254Notes

Reaction equation

HRID 1464254 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

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

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 hours
  3. filtrationAfter the resultant salt was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Waco Gel C-200, 200 g)
  6. washeluted with a mixed solvent of chloroform (99 parts)+methanol (1 part)

Sources & evidence

ORD record
ord-e4435c199ae14731bf73db7d7a2803b9
Source dataset
uspto-grants-1994_04
Patent number
US05304558

Reaction notes

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