Methyl (4-ethylpiperazin-1-YL)acetate → (4-ethylpiperazin-1-yl)acetic acid
Reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]([O:12]C)=[O:11])[CH2:5][CH2:4]1)[CH3:2]>Cl>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]([OH:12])=[O:11])[CH2:5][CH2:4]1)[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The solution of methyl 2-(4-ethylpiperazin-1-yl)acetate (1.3 g, 6.50 mmol, 1.0 eq) in 8 N HCl was stirred at 95° C. for 16 h and concentrated on vacuum pump. The mixture was quenched with sodium bicarbonate solution and extracted with ethyl acetate (3×150 ml). The combined organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to give the product in 54.5% yield (0.6 g). LC-MS (ESI): Calculated mass: 158.0; Observed mass: 159.1 [M+H]+ (rt: 0.102 min).
Workup
- concentrationconcentrated on vacuum pump
- customThe mixture was quenched with sodium bicarbonate solution
- extractionextracted with ethyl acetate (3×150 ml)
- washThe combined organic layer was washed with water, brine
- dry with materialdried over sodium sulphate
- distillationThe solvent was distilled off
- customto give the product in 54.5% yield (0.6 g)
- custom159.1 [M+H]+ (rt: 0.102 min)
Sources & evidence
- ORD record
- ord-4544f572bade4515a070798b53bfd761
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447091B2
Reaction notes
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