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

HRID 1161862

Reaction equation

C([N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][CH2:10][NH2:11])C1C=CC=CC=1.C(N(CC)CC)C.[CH2:26]([O:28][C:29](=[O:33])[CH:30](Br)[CH3:31])[CH3:27].[C:34]1([CH3:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:26]([O:28][C:29]([CH:30]1[CH2:31][N:8]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9][CH2:10][N:11]1[CH2:40][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33])[CH3:27]

Participants

Reactant 4

HCID 1140Toluene2×

HCID 8471Triethylamine

HCID 79040Ethyl 2-bromopropionate

HCID 6394114N1,N1-Dibenzylethane-1,2-diamine

Product 1

HCID 2736402Ethyl 1,4-dibenzylpiperazine-2-carboxylateYield 96%

Conditions

Temperature: 80 °C

Procedure

A solution of N,N-dibenzylethylenediamine (980 μL, 4.10 mmol) and triethylamine (1.03 mL, 7.38 mmol) in toluene (15 mL) was added dropwise to a solution of 2-bromopropionic acid ethyl ester (601 μL, 4.14 mmol) in toluene (15 mL). The reaction mixture was stirred at 80° C. for 72 h. The reaction mixture was filtered through a pad of celite and solvent evaporated under reduced pressure to afford 1,4-dibenzylpiperazine-2-carboxylic acid ethyl ester (1.33 g, 3.93 mmol, 96%) as a yellow oil.

Workup

filtrationThe reaction mixture was filtered through a pad of celite and solvent
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-38b6c756ab61492fbf41aaf05fc15f7e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820649B2

Linked notes

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