Hydrochloric Acid → HCID 20510930, compound

HRID 1758130Notes

Reaction equation

HRID 1758130 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(CC)CC)C.C([N:25]1[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:28]([CH2:35]Br)[NH:27][C:26]1=[O:37])(=O)C.[ClH:38]>C(O)C>[ClH:38].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:35][C:28]2[NH:27][C:26](=[O:37])[NH:25][C:29]=2[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13461-(2-Methoxyphenyl)piperazineHCID 8471TriethylamineHCID 12850294HCID 12850294, compound

Product 1

HCID 20510930HCID 20510930, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution (0° C.) of 2 g of 1-(2-methoxyphenyl)piperazine and 2.1 g of triethylamine in 40 ml of ethanol is added 2.9 g of ethyl 3-acetyl-5-(bromomethyl)-2,3-dihydro-2-oxo-1H-imidazole-4-carboxylate. The resulting solution is stirred at 0° C. for 4 hours, 30 ml of ice-water is added and the mixture is filtered. One equivalent of hydrochloric acid is added to the filtrate and it is evaporated to dryness. The residue crystallizes from a mixture of ethanol and ethyl acetate (1:1) and is recrystallized from that solvent mixture to give ethyl 2,3-dihydro-5-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-2-oxo-1H-imidazole-4-carboxylate hydrochloride melting at about 227° C. (dec.). The free base of this compound has the following structural formula: ##STR6##

Workup

  1. filtrationthe mixture is filtered
  2. customis evaporated to dryness
  3. customThe residue crystallizes from a mixture of ethanol and ethyl acetate (1:1)
  4. customis recrystallized from that solvent mixture

Sources & evidence

ORD record
ord-5bb4d4b78b384f6dae1386e5e186f748
Source dataset
uspto-grants-1983_02
Patent number
US04371737

Reaction notes

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