Glycidol → HCID 22721094, compound

HRID 1582474Notes

Reaction equation

HRID 1582474 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:11]([C:20]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[O:21])[C:10]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=3[O:36][CH:37]([CH3:39])[CH3:38])=[N:9]2)=[CH:4][CH:3]=1.[CH2:40]1[O:42][CH:41]1[CH2:43][OH:44]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:11]([C:20]([N:22]3[CH2:23][CH2:24][N:25]([CH2:40][CH:41]([OH:42])[CH2:43][OH:44])[CH2:26][CH2:27]3)=[O:21])[C:10]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=3[O:36][CH:37]([CH3:39])[CH3:38])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11164GlycidolHCID 22721056HCID 22721056, compound

Product 1

HCID 22721094HCID 22721094, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

[4,5-Bis-(4-chloro-phenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazol-1-yl]-piperazin-1-yl-methanone (50 mg, 0.088 mmol, example 10 g) was dissolved in anhydrous methanol (10 mL). Glycidol (0.15 mL, 2.26 mmol) was added and the reaction was heated at 40° C. for 20 h. The mixture was cooled to room temperature and concentrated in vacuo. Chromatography of the residue over silica gel using 1-6% methanol in methylene chloride gave [4,5-bis-(4-chloro-phenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-(2,3-dihydroxy-propyl)-piperazin-1-yl]-methanone (25 mg, 44%). HR-MS (ES, m/z) calculated for C33H39N4O5Cl2[(M+H)+]641.2292, observed 641.2300.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c70894ee0a4d40e4b4c5b2b2bae3a98d
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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