Hydrochloric Acid → HCID 20540670, compound

HRID 1065503Notes

Reaction equation

HRID 1065503 reaction equation
C([N:4]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([CH2:14]Br)[NH:6][C:5]1=[O:16])(=O)C.[C:17]1([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[ClH:35]>CC(O)C.O.C(O)C>[ClH:35].[C:17]1([CH:23]2[CH2:24][CH2:25][N:26]([CH2:14][C:7]3[NH:6][C:5](=[O:16])[NH:4][C:8]=3[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:27][CH2:28]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 12850294HCID 12850294, compound

Product 1

HCID 20540670HCID 20540670, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4.4 g (15 mmole) of ethyl 3-acetyl-5-(bromomethyl)-2,3-dihydro-2-oxo-1H-imidazole-4-carboxylate 2.5 g (16 mmole) of 4-phenylpiperidine, 2.1 g (15 mmole) of potassium carbonate and 75 ml of ethanol is stirred at 25° C. for 16 hours. Water (100 ml) is added and a precipitate forms. This is separated by filtration and washed with water. It is then suspended in 2-propanol and 1 equivalent of hydrogen chloride in 2-propanol is added. The resulting solid is separated by filtration and recrystallized from 2-propanol containing a little water to give ethyl 2,3-dihydro-5-[(4-phenyl-1-piperidinyl)methyl]-2-oxo-1H-imidazole-4-carboxylate hydrochloride melting at about 240°-241° C.

Workup

  1. customThis is separated by filtration
  2. washwashed with water
  3. customThe resulting solid is separated by filtration
  4. customrecrystallized from 2-propanol containing a little water

Sources & evidence

ORD record
ord-57f7087074164b069432ef18df32149a
Source dataset
uspto-grants-1982_05
Patent number
US04329470

Reaction notes

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