1-(2-Methoxyphenyl)piperazine → 5-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]-3-methyl-2-oxazolidinone dihydrochloride

HRID 373014Notes

Reaction equation

HRID 373014 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:10][C:9](=[O:11])[N:8]([CH3:12])[CH2:7]1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC>[ClH:1].[ClH:1].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][CH2:4][CH2:5][CH:6]2[O:10][C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 198114625-(4-Chlorobutyl)-3-methyl-2-oxazolidinone

Product 1

HCID 198114675-[4-[4-(2-Methoxyphenyl)-1-piperazinyl]butyl]-3-methyl-2-oxazolidinone dihydrochlorideYield 38%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Following the procedures of Example 1, the title compound is prepared. Thus, a mixture of 5-(4-chlorobutyl)-3-methyl-2-oxazolidinone (5.0 g, 0.0262 mol), 1-(2-methoxyphenyl)piperazine (5.4 g. 0.0279 mol), potassium carbonate (8.5 g, 0.0614 mol), and potassium iodide (0.75 g) in 1-butanol (50 ml) gave 6.8 g of oil which was dissolved in hot methanol and acidified with methanolic hydrogen chloride. Addition of isopropyl ether and isopropanol to the cloud point and cooling gave a solid which was collected by filtration, rinsed with isopropyl ether and light pet ether and dried under high vacuum to give 4.22 g (38% yield), mp 209°-216° C.

Sources & evidence

ORD record
ord-63013931335242548a8052cad887e725
Source dataset
uspto-grants-1992_11
Patent number
US05162322

Reaction notes

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