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

HRID 2287341Notes

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+]>[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 ml) 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.

Workup

customThe solvent was evaporated off in vaccuo
extractionextracted with chloroform (3×40 ml)
washwashed with water (2×40 ml)
dry with materialdried over anhydrous Na2SO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-40aafda72eb54d818a8ef1fdef05e4b9
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06083950

Reaction notes

Loading…