Water → Ethyl 4-(2-carbamoylmethoxyethyl)piperazine-1-carboxylate

HRID 1383753Notes

Reaction equation

HRID 1383753 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][C:6]([NH2:8])=[O:7].[N:9]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.[I-].[K+].C(O)(C)C>[C:6]([CH2:5][O:4][CH2:3][CH2:2][N:12]1[CH2:11][CH2:10][N:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][CH2:13]1)(=[O:7])[NH2:8]

Participants

8

Reactant 4

HCID 962WaterHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 10340Sodium CarbonateHCID 110189312-(2-Chloroethoxy)acetamide

Product 1

HCID 21188378Ethyl 4-(2-carbamoylmethoxyethyl)piperazine-1-carboxylateYield 82.3%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

15.13 g of (2-chloroethoxy)acetamide (0.11 mol), 14.6 ml of ethyl piperazine carboxylate (0.1 mol), 23.3 g of sodium carbonate (0.22 mol) and 1.0 g of potassium iodide in 25 ml of toluene are introduced into a round-bottomed flask fitted with a water-cooled condenser and a mechanical stirrer. The mixture is heated at the reflux temperature for 4 hours and is allowed to cool to room temperature. The reaction is continued, still with stirring, for a further 16 hours. 100 ml of isopropanol are added and the solid materials formed are filtered off. The solvent is evaporated from the filtrate under reduced pressure to dryness. The product obtained after evaporation of the solvents is recrystallized from toluene. 21.35 g of ethyl 4-(2-carbamoylmethoxyethyl)piperazine-1-carboxylate are obtained. Yield: 82%. Mass spectrum: 260 (MH+), 214 (M+−OEt).

Workup

  1. temperaturecooled condenser and a mechanical stirrer
  2. temperatureThe mixture is heated at the reflux temperature for 4 hours
  3. customthe solid materials formed
  4. filtrationare filtered off
  5. customThe solvent is evaporated from the filtrate under reduced pressure to dryness
  6. customThe product obtained
  7. customafter evaporation of the solvents
  8. customis recrystallized from toluene

Sources & evidence

ORD record
ord-453d91fe6e56431e8f6fb19b2bde1b77
Source dataset
uspto-grants-2001_07
Patent number
US06255487B1

Reaction notes

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