Hydrochloric Acid → HCID 20540680, compound

HRID 1065504Notes

Reaction equation

HRID 1065504 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.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([OH:30])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(O)C.O.C(O)C>[ClH:17].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([OH:30])[CH2:25][CH2:26][N:27]([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])[CH2:28][CH2:29]2)=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 12850294HCID 12850294, compound

Product 1

HCID 20540680HCID 20540680, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4.1 g (14.2 mmole) of ethyl 3-acetyl-5-(bromomethyl)-2,3-dihydro-2-oxo-1H-imidazole-4-carboxylate, 3.0 g (14.2 mmole) of 4-(4-chlorophenyl)-4-hydroxypiperidine, 2.0 g (14.2 mmole) of potassium carbonate and 75 ml of ethanol is stirred under argon for 16 hours at 25° C. Water (100 ml) is added and the precipitate which forms is collected 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 and recrystallized twice from a mixture of 2-propanol and water to give ethyl 5-[[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]methyl]-2,3-dihydro-2-oxo-1H-imidazole-4-carboxylate hydrochloride.

Workup

  1. customthe precipitate which forms is collected
  2. washwashed with water
  3. customThe resulting solid is separated
  4. customrecrystallized twice from a mixture of 2-propanol and water

Sources & evidence

ORD record
ord-7752f95161124449bc8101678b9422fd
Source dataset
uspto-grants-1982_05
Patent number
US04329470

Reaction notes

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