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

HRID 37189
Notes
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Reaction equation

HRID 37189 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 19934805HCID 19934805, compound

Product 1

HCID 199348062-[3-[4-[[5-Methyl-2-(1-methylethyl)phenoxy]methyl]piperid-1-yl]propyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. additionIt is poured into ice-cold water
  2. extractionThe solution is extracted with ethyl acetate and it
  3. washis washed with water
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes