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

HRID 373030Notes

Reaction equation

HRID 373030 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.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>C(O)CCC.C(O)C.CCOCC>[ClH:1].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][N:26]([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)[CH2:25][CH2:24]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 13461-(2-Methoxyphenyl)piperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 198114795-(4-Chlorobutyl)-3-(1-methylethyl)-2-oxazolidinone

Product 1

HCID 198114705-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]-3-(1-methylethyl)-2-oxazolidinone hydrochlorideYield 69%

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 (5.2 g, 0.0237 mol), 1-(2-methoxyphenyl)piperazine (4.56 g, 0.0237 mol), potassium carbonate (9.84 g, 0.0712 mol) and potassium iodide (1.0 g) in n-butanol (200 mL) gave an oil. The oil was dissolved in absolute ethanol and acidified with ethanolic hydrogen chloride. Addition of ether gave a solid which was collected by filtration and dried under high vacuum at 70° C. to give 7.36 g (69% yield), mp 206°-213° C.

Workup

  1. customgave an oil
  2. customgave a solid which
  3. filtrationwas collected by filtration
  4. customdried under high vacuum at 70° C.
  5. customto give 7.36 g (69% yield), mp 206°-213° C.

Sources & evidence

ORD record
ord-f8de769a5bfd4f779789a56db763818d
Source dataset
uspto-grants-1992_11
Patent number
US05162322

Reaction notes

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