Potassium Phosphate, Tribasic → HCID 70874566, compound

HRID 2172180Notes

Reaction equation

HRID 2172180 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][CH:12]2[CH2:14][O:13]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)[CH3:23])=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(O)C>[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][CH:12]([OH:13])[CH2:14][O:36][C:33]2[CH:32]=[CH:31][C:30]([N:27]3[CH2:26][CH2:25][CH:24]([N:22]([C:19]4[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=4)[CH3:23])[CH2:29][CH2:28]3)=[CH:35][CH:34]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 67274595HCID 67274595, compoundHCID 86650544HCID 86650544, compound

Product 1

HCID 70874566HCID 70874566, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

2-Chloro-4-nitro-1-(2-oxiranylethyl)-1H-imidazole (810 mg) was suspended in ethanol (20 ml) and 4-{4-[N-(4-chlorophenyl)-N-methylamino]piperidin-1-yl}phenol (982 mg) and tripotassium phosphate (200 mg) were added thereto, followed by stirring at 70° C. overnight. Thereafter the reaction solution was cooled to room temperature, and filtered through Celite to remove insoluble matter and, then the residue was washed with ethyl acetate. The filtrate and liquid were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:1) and recrystallized from methylene chloride-ethyl acetate to afford the title compound as a yellow solid (486 mg).

Workup

  1. temperatureThereafter the reaction solution was cooled to room temperature
  2. filtrationfiltered through Celite
  3. customto remove insoluble matter
  4. washthe residue was washed with ethyl acetate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:1)
  7. customrecrystallized from methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-916454f7f4254a5f839874f989bf727c
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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