Potassium Iodide → Ethyl (2-carbamoylmethoxyethyl)piperazine-1-carboxylate

HRID 1383752Notes

Reaction equation

HRID 1383752 reaction equation
[N:1]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:13][CH2:14][O:15][CH2:16][C:17]([NH2:19])=[O:18].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)(C)C.O.C1(C)C=CC=CC=1>[C:17]([CH2:16][O:15][CH2:14][CH2:13][CH:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:1]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:18])[NH2:19]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 10340Sodium CarbonateHCID 110189312-(2-Chloroethoxy)acetamide

Product 1

HCID 53803652Ethyl (2-carbamoylmethoxyethyl)piperazine-1-carboxylateYield 81.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

164 g (1.04 mol) of ethyl piperazinecarboxylate, 156.9 g (1.14 mol) of (2-chloroethoxy)acetamide, 241.7 g (2.28 mol) of sodium carbonate, 1g of potassium iodide and 200 ml of toluene are introduced into a 2 l three-necked round-bottomed flask fitted with a water-cooled condenser and a mechanical stirrer. The mixture is brought at the reflux temperature for 3 hours 30. The mixture is allowed to cool to 50° C., and 200 ml of isopropanol are added. The reaction mixture is filtered and the filtration residue is washed with 150 ml of isopropanol. The filtrate is concentrated on a rotary evaporator under reduced pressure. 277.2 g of crude product are obtained, which product is recrystallized from 500 ml of ethyl acetate. 219.2 g (81.6%) of ethyl (2-carbamoylmethoxyethyl)piperazine-1-carboxylate are obtained in the form of a white solid. NMR: δ: 1.24 (3H, t, 7.05 Hz); 2.46 (4H, m); 2.57 (2H, t, 5.2 Hz); 3.44 (4H, m); 3.62 (2H, t, 5.2 Hz); 3.95 (2H, s); 4.1 (2H, 9, 7.1 Hz); 5.72 (1H, bs); 7.34 (1H, bs). Mass spectrum: 260 (MH+). DSC: Onset 106.5° C., Max: 109.7° C. Elemental analysis:

Workup

  1. temperaturecooled condenser and a mechanical stirrer
  2. filtrationThe reaction mixture is filtered
  3. washthe filtration residue is washed with 150 ml of isopropanol
  4. concentrationThe filtrate is concentrated on a rotary evaporator under reduced pressure
  5. custom277.2 g of crude product are obtained
  6. customwhich product is recrystallized from 500 ml of ethyl acetate

Sources & evidence

ORD record
ord-8ac7a9df8a5d4e929cf9d18ed008b11d
Source dataset
uspto-grants-2001_07
Patent number
US06255487B1

Reaction notes

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