Methyl (4-ethylpiperazin-1-yl)acetate → (4-ethylpiperazin-1-yl)acetic acid

HRID 64061Notes

Reaction equation

HRID 64061 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

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

  1. concentrationconcentrated on vacuum pump
  2. customThe mixture was quenched with sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (3×150 ml)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over sodium sulphate
  6. distillationThe solvent was distilled off
  7. customto give the product in 54.5% yield (0.6 g)
  8. 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

Loading…