Hydrochloric Acid → 3-{4-[3-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)-propoxy]-3-hydroxymethyl-5-methoxy-phenyl}oxazolidin-2-one hydrochloride

HRID 655672Notes

Reaction equation

HRID 655672 reaction equation
[ClH:1].[S:2]1[CH:6]=[CH:5][C:4]2[C:7]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]4[C:28]([O:29][CH3:30])=[CH:27][C:26]([N:31]5[CH2:35][CH2:34][O:33][C:32]5=[O:36])=[CH:25][C:22]=4[CH:23]=[O:24])[CH2:13][CH2:12]3)=[CH:8][CH:9]=[CH:10][C:3]1=2.Cl.[K].[BH4-].[Na+].Cl.[OH-].[Na+]>>[ClH:1].[S:2]1[CH:6]=[CH:5][C:4]2[C:7]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]4[C:28]([O:29][CH3:30])=[CH:27][C:26]([N:31]5[CH2:35][CH2:34][O:33][C:32]5=[O:36])=[CH:25][C:22]=4[CH2:23][OH:24])[CH2:13][CH2:12]3)=[CH:8][CH:9]=[CH:10][C:3]1=2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 574996172-[3-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-(2-oxo-oxazolidin-3-yl)benzaldehyde hydrochlorideHCID 86590535Potassium hydrochloride

Product 1

HCID 574996153-{4-[3-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)-propoxy]-3-hydroxymethyl-5-methoxy-phenyl}oxazolidin-2-one hydrochlorideYield 41%

Procedure

First, 2-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-(2-oxo-oxazolidin-3-yl)benzaldehyde hydrochloride (1.28 g. 2.4 mmol)) was added to an aqueous potassium hydrochloride solution. The mixture was extracted with dichloromethane. The extracted solution was concentrated under reduced pressure and the residue was dissolved in THF (15 ml). To the solution, sodium borohydride (0.05 g, 1.2 mmol) was added under ice cooling and the mixture was stirred at room temperature for 3 hours. Then, 10% hydrochloric acid was added to the mixture under ice cooling to decompose the reagent excessively present. After an aqueous 6N sodium hydroxide solution was added to the solution to make it an alkaline solution, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and thereafter concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=3:7→dichloromethane:methanol=100:3). The purified product was concentrated under reduced pressure and the residue was dissolved in ethanol. A 1N hydrochloric acid/ethanol solution was added to this. The crystal produced was recrystallized from ethanol to obtain 3-{4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)-propoxy]-3-hydroxymethyl-5-methoxy-phenyl}oxazolidin-2-one hydrochloride (0.52 g, 41% yield) as white powder.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. concentrationThe extracted solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in THF (15 ml)
  4. extractionwas then extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=3:7→dichloromethane:methanol=100:3)
  8. concentrationThe purified product was concentrated under reduced pressure
  9. dissolutionthe residue was dissolved in ethanol
  10. additionA 1N hydrochloric acid/ethanol solution was added to this
  11. customThe crystal produced
  12. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-817c45823d9f4711852469287aaffac4
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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