Potassium Carbonate → HCID 57531251, compound

HRID 1454988Notes

Reaction equation

HRID 1454988 reaction equation
Cl.[N:2]1([C:8]([O:10][CH2:11][C:12]([NH:14][CH3:15])=[O:13])=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1>C(#N)C>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][N:5]2[CH2:6][CH2:7][N:2]([C:8]([O:10][CH2:11][C:12]([NH:14][CH3:15])=[O:13])=[O:9])[CH2:3][CH2:4]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 748541-(2-Bromoethoxy)-4-chlorobenzeneHCID 60209555HCID 60209555, compound

Product 1

HCID 57531251HCID 57531251, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.073 g (0.3 mmol) of 2-(methylamino)-2-oxoethyl piperazine-1-carboxylate hydrochloride, prepared in step 3.3., 0.13 g (0.9 mmol) of potassium carbonate and 0.069 g (0.29 mmol) of 1-(2-bromoethoxy)-4-chlorobenzene in 3 ml of acetonitrile is heated at 85° C. for 16 hours. After cooling to ambient temperature, the inorganic components are filtered off through a cartridge fitted with a frit and containing celite. The cartridge is rinsed with acetone and the filtrate is concentrated under reduced pressure. Chromatography on silica gel, eluting with a 95/5 mixture of dichloromethane and methanol, followed by crystallization from diisopropyl ether give 0.089 g of product in the form of a white solid.

Workup

  1. filtrationthe inorganic components are filtered off through a cartridge
  2. customfitted with a frit
  3. additioncontaining celite
  4. washThe cartridge is rinsed with acetone
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. washChromatography on silica gel, eluting with a 95/5 mixture of dichloromethane and methanol
  7. customfollowed by crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-e813eb82aece4ddd89a7c455b7473b02
Source dataset
uspto-grants-2009_01
Patent number
US07482346B2

Reaction notes

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