Piperazine → N-(4,5-diphenyloxazolyl)methyl piperazine

HRID 1769685Notes

Reaction equation

HRID 1769685 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18]Br)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C(O)C>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 5685992-Bromomethyl-4,5-diphenyl-oxazole

Product 1

HCID 214431N-(4,5-diphenyloxazolyl)methyl piperazineYield 98.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,5-diphenyl-2-bromomethyloxazole (X; 20 g, 0.063 moles) and excess piperazine (10 mol equivalent) in 400 ml of absolute ethanol was stirred overnight at room temperature. The reaction mixture was evaporated and the residue was taken up in 4X200 ml of methylene chloride and washed several times with water and brine. The organic layer was dried over Na2SO4, evaporated and the product was obtained as a yellow solid (19.8 g, 95%) after passing through a silica gel column and eluting with a mixture of methanol/chloroform (1:9). This procedure is amenable for large scale synthesis. MS (DCl) MH+ 320.

Workup

  1. customThe reaction mixture was evaporated
  2. washwashed several times with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-d96bb9843a674c42b9691b288054e724
Source dataset
uspto-grants-1995_01
Patent number
US05382584

Reaction notes

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