Benzathine → Ethyl 1,4-dibenzylpiperazine-2-carboxylate

HRID 524776Notes

Reaction equation

[CH2:1]([NH:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:20]([CH2:26]Br)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:26][CH:20]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N1,N2-dibenzylethane-1,2-diamine (24 g, 100 mmol) in toluene (100 mL) was added TEA (24.2 g, 240 mmol). The mixture was heated to 80° C., and a solution of ethyl 2,3-dibromopropanoate (27.3 g, 105 mmol) in toluene (100 mL) was added dropwise over a period of 0.5 hour at 80° C. Then the mixture was stirred at the temperature for 12 hours and cooled to 25° C. The reaction mixture was washed with saturated NaHCO3 aqueous solution. The organic layer was dried over Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=5/1) to give the title compound as yellow oil (22.7 g, 67%). The compound was characterized by the following spectroscopic data:

Workup

temperaturecooled to 25° C
washThe reaction mixture was washed with saturated NaHCO3 aqueous solution
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=5/1)

Sources & evidence

ORD record: ord-b4a8d81a60aa42efa0511ed7d95ad656
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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