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

HRID 373019Notes

Reaction equation

HRID 373019 reaction equation
Br.Br.[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Cl[CH2:17][CH2:18][CH2:19][CH:20]1[O:24][C:23](=[O:25])[N:22]([CH3:26])[CH2:21]1.C(=O)(O)[O-].[Na+].[I-].[K+]>C(O)CCC>[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:17][CH2:18][CH2:19][CH:20]2[O:24][C:23](=[O:25])[N:22]([CH3:26])[CH2:21]2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 3017100o-(1-Piperazinyl)phenol dihydrobromideHCID 198114995-(3-Chloropropyl)-3-methyl-2-oxazolidinone

Product 1

HCID 198114765-[3-[4-(2-Hydroxyphenyl)-1-piperazinyl]propyl]-3-methyl-2-oxazolidinoneYield 20%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Following the procedure of Example 5, a mixture of 1-(2-hydroxyphenyl)piperazine dihydrobromide (9.6 g, 0.0282 mol), 5-(3-chloropropyl)-3-methyl-2-oxazolidinone (5.0 g, 0.0282 mol), sodium bicarbonate (9.5 g, 0.113 mol), and potassium iodide in 1-butanol (100 ml) gave an oil. The oil was triturated several times with light pet ether (decanting each time) and dissolved in ethyl acetate/isopropyl ether. Cooling the solution gave a solid which was collected by filtration and dried under high vacuum to give 1.80 g (20% yield), mp 112°-116° C.

Workup

  1. customgave an oil
  2. customThe oil was triturated several times with light pet ether (
  3. customdecanting each time) and
  4. dissolutiondissolved in ethyl acetate/isopropyl ether
  5. temperatureCooling the solution
  6. customgave a solid which
  7. filtrationwas collected by filtration
  8. customdried under high vacuum
  9. customto give 1.80 g (20% yield), mp 112°-116° C.

Sources & evidence

ORD record
ord-27186ddf7f3f4aea989e251c0c238511
Source dataset
uspto-grants-1992_11
Patent number
US05162322

Reaction notes

Loading…