1-Phenylpiperazine → 1-Piperazineacetic acid, 4-phenyl-, ethyl ester

HRID 1406674Notes

Reaction equation

HRID 1406674 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])(O)=O.[Na+]>CC(C)=O>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 7751Ethyl chloroacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 30442591-Piperazineacetic acid, 4-phenyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Synthesized according to General Procedure B: 1-phenylpiperazine (5{30}, 1 mL, 6.55 mmol, 1 equiv.), ethyl chloroacetate (0.77 mL, 7.20 mmol, 1.1 equiv.), NaHCO3 (0.69 g, 8.18 mmol, 1.25 equiv.), acetone (13.1 mL). Purification with flash column chromatography on silica gel (1:1 hexanes:EtOAc) afforded 6{30} (1.50 g, 93%) as a light yellow liquid. 1H-NMR (500 MHz, CDCl3): δ 7.20 (dd, 2H, J=7.0, 8.5 Hz), 6.87 (dd, 2H, J=1.0, 9.0 Hz), 6.80 (t, 1H, J=7.0 Hz), 4.15 (q, 2H, J=7.0 Hz), 3.20 (s, 2H), 3.19 (t, 4H, J=5.0 Hz), 2.68 (t, 4H, J=5.0 Hz), 1.23 (t, 3H, J=7.0 Hz). 13C-NMR (125 MHz, CDCl3): δ 169.6, 150.8, 128.6, 119.2, 115.6, 60.1, 58.9, 52.5, 48.5, 13.8.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (1:1 hexanes:EtOAc)
  3. customafforded 6{30} (1.50 g, 93%) as a light yellow liquid

Sources & evidence

ORD record
ord-25200d4c123b4c54ab80804c59e23d62
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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