Chloroform → 2,6-Piperidinedione, 1-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]-

HRID 2229154Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Scheme-I: A mixture of 2,6-dioxopiperidine (2.60 g, 23.02 mmol), 1-[4-(2-methoxyphenyl)-piperazin-1-yl]-3-chloropropane (6.18 g, 23.02 mmol), potassium carbonate (2.38 g, 17.27 mmol) and tetrabutylammonium bromide (1.48 g, 4.60 mmol) in acetone (80 ml) was refluxed for 16 hours at 80° C. with stirring. The solvent was evaporated off in vaccuo and the residue suspended in water (60 ml), extracted with chloroform (3×40 mmol) and the organic layers combined, washed with water (2.40 ml), dried over anhydrous Na2SO4 and evaporated in vacuo to give the title compound. The product was purified by column chromatography over flash silica gel (230-400 mesh) using chloroform-methanol (98:1) as eluent; yield 3.58 g (45%), oil. The hydrochloride salt was prepared in the quantitative yield by the method described above; m.p. 206-210° C.

Workup

customThe solvent was evaporated off in vaccuo
washwashed with water (2.40 ml)
dry with materialdried over anhydrous Na2SO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-e531d11a92bf4d65838d58d156581b66
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420366B1

Reaction notes

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