Potassium Iodide → 5-[4-[4-(2-Hydroxyphenyl)-1-piperazinyl]butyl]-3-phenyl-2-oxazolidinone

HRID 373025Notes

Reaction equation

HRID 373025 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1.Br.Br.[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(=O)(O)[O-].[Na+].[I-].[K+]>C(O)CCC>[OH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][CH2:5][CH:6]2[O:10][C:9](=[O:11])[N:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7]2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 3017100o-(1-Piperazinyl)phenol dihydrobromideHCID 198115005-(4-Chlorobutyl)-3-phenyl-2-oxazolidinone

Product 1

HCID 198114815-[4-[4-(2-Hydroxyphenyl)-1-piperazinyl]butyl]-3-phenyl-2-oxazolidinoneYield 112%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Following the procedure of Example 5, a mixture of 5-(4-chlorobutyl)-3-phenyl-2-oxazolidinone (6.0 g, 0.0237 mol), 1-(2-hydroxyphenyl)piperazine dihydrobromide (8.06 g, 0.0237 mol), sodium bicarbonate (7.98 g, 0.095 mol), and potassium iodide (1.0 g) in n-butanol (200 mL) gave an oil (10.5 g) which crystallized on standing and was recrystallized from isopropanol/isopropyl ether. Drying under high vacuum gave 6.15 g (66% yield), mp 123°-129° C.

Sources & evidence

ORD record
ord-39a0043b243d44639258aa41ab276f11
Source dataset
uspto-grants-1992_11
Patent number
US05162322

Reaction notes

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