Hydrochloric Acid → 5-[4-[4-(2-Hydroxyphenyl)-1-piperazinyl]butyl]-3-(1-methylethyl)-2-oxazolidinone hydrochloride

HRID 373032Notes

Reaction equation

HRID 373032 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:10][C:9](=[O:11])[N:8]([CH:12]([CH3:14])[CH3:13])[CH2:7]1.Br.Br.[OH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+].[I-].[K+].Cl>C(O)CCC.C(O)C.CCOCC>[ClH:1].[OH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][CH2:4][CH2:5][CH:6]2[O:10][C:9](=[O:11])[N:8]([CH:12]([CH3:14])[CH3:13])[CH2:7]2)[CH2:26][CH2:25]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 3017100o-(1-Piperazinyl)phenol dihydrobromideHCID 198114795-(4-Chlorobutyl)-3-(1-methylethyl)-2-oxazolidinone

Product 1

HCID 198114545-[4-[4-(2-Hydroxyphenyl)-1-piperazinyl]butyl]-3-(1-methylethyl)-2-oxazolidinone hydrochlorideYield 46%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Following the procedure of Example 5, a mixture of 5-(4-chlorobutyl)-3-(1-methylethyl)-2-oxazolidinone (10.4 g, 0.0474 mol), 1-(2-hydroxyphenyl)piperazine dihydrobromide (16.12 g, 0.0474 mol), sodium bicarbonate (15.96 g, 0.190 mol) and potassium iodide (1.0) in n-butanol (350 mL) gave an oil. The oil was dissolved in absolute ethanol and acidified with ethanolic hydrogen chloride. Addition of ether and filtration gave a solid which was dried under high vacuum at 70° C. to give 9.47 g (46% yield), mp 203°-207° C.

Workup

  1. customgave an oil
  2. customgave a solid which
  3. customwas dried under high vacuum at 70° C.
  4. customto give 9.47 g (46% yield), mp 203°-207° C.

Sources & evidence

ORD record
ord-46672f5ef28a4f7e8c87481a86a888e2
Source dataset
uspto-grants-1992_11
Patent number
US05162322

Reaction notes

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