Reaction equation
[CH2:1]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:16]([C:23]([O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:4]1(/[CH:3]=[CH:2]/[CH2:1][N:10]2[CH2:15][CH2:14][N:13]([C:23]([O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:16])[CH2:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1.40 g (6.93 mmol) of trans-1-cinnamylpiperazine and 1.74 g (7.76 mmol) of ethyl {[(phenoxy)carbonyl]oxy}acetate (J. Med. Chem., 1999, 42, 277-290) in 15 ml of toluene is heated at 80° C. overnight. It is evaporated to dryness and the residue is taken up in 50 ml of ethyl acetate. It is washed with 2 times 20 ml of water and 1 times 10 ml of saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with a 50/50 mixture of cyclohexane and ethyl acetate, then with ethyl acetate, to give 0.814 g of product in the form of a pale yellow oil.
Workup
- customIt is evaporated to dryness
- washIt is washed with 2 times 20 ml of water and 1 times 10 ml of saturated aqueous sodium chloride solution
- dry with materialIt is dried over sodium sulphate
- customevaporated to dryness
- customThe residue is purified by chromatography on silica gel
- washeluting with a 50/50 mixture of cyclohexane and ethyl acetate
Sources & evidence
- ORD record
- ord-b1397f410868479aa15d4bd8566d6a76
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973042B2
Linked notes
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