Triethylamine → Ethyl 1,4-dibenzylpiperazine-2-carboxylate
Reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH:5](Br)[CH2:6]Br)[CH3:2].[CH2:10]([NH:17][CH2:18][CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:5]1[CH2:6][N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:19][CH2:18][N:17]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2,3-dibromopropionic acid ethyl ester (21.91 ml, 150.7 mmol) in toluene (175 ml) at 40° C. was added a mixture of N,N′-dibenzylethylenediamine (35.87 g, 149.2 mmol) and triethylamine (37 ml, 269 mmol) in toluene (75 ml). The mixture was heated to 80° C. for 16 h, filtered and the precipitate washed with toluene (200 ml). The combined filtrates were washed with water (2×200 ml), dried with magnesium sulfate and evaporated to afford 1,4-dibenzyl-piperazine-2-carboxylic acid ethyl ester (45.57 g) as an orange oil.
Workup
- filtrationfiltered
- washthe precipitate washed with toluene (200 ml)
- washThe combined filtrates were washed with water (2×200 ml)
- dry with materialdried with magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-cd32d5dc6f92446eab25be8adc222766
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07304064B2
Reaction notes
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