Potassium Carbonate → 2-[3-[4-[[5-Methyl-2-(1-methylethyl)phenoxy]methyl]piperid-1-yl]propyl]-1H-isoindole-1,3(2H)-dione

HRID 37189Notes

Reaction equation

Cl.[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH:17]([CH3:19])[CH3:18])=[C:7]([CH:16]=1)[O:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Br[CH2:21][CH2:22][CH2:23][N:24]1[C:32](=[O:33])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]1=[O:34].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH:17]([CH3:19])[CH3:18])=[C:7]([CH:16]=1)[O:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:21][CH2:22][CH2:23][N:24]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]2=[O:34])[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

11.35 g (0.04 mol) of 4-[[5-methyl-2-(1methylethyl)phenoxy]methyl]piperidine hydrochloride, 10.72 g (0.04 mol) of 2-(3-bromopropyl)-1H-isoindole-1,3(2H)-dione and 13.8 g (0.1 mol) of potassium carbonate are reacted in 113 ml of N,N-dimethylformamide. The mixture is stirred for 3 h at 100° C. It is poured into ice-cold water. The solution is extracted with ethyl acetate and it is washed with water. The organic phase is dried over sodium sulphate, filtered and concentrated under reduced pressure. The product obtained is used as is in the following stage.

Workup

additionIt is poured into ice-cold water
extractionThe solution is extracted with ethyl acetate and it
washis washed with water
dry with materialThe organic phase is dried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe product obtained

Sources & evidence

ORD record: ord-64f3955d8a51403ab6446bc3f2373b4e
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420130

Reaction notes

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