Potassium Carbonate → N-(6-[4-(Morpholinomethyl)phenoxy]hexyl)phthalimide

HRID 2097369Notes

Reaction equation

HRID 2097369 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]3[C:26](=[O:27])[C:25]4=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]4[C:23]3=[O:32])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 141120N-(6-Bromohexyl)phthalimideHCID 7833224-(Morpholinomethyl)phenol

Product 1

HCID 23132451N-(6-[4-(Morpholinomethyl)phenoxy]hexyl)phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(morpholinomethyl)phenol (776 mg, 4.0 mmol) and N-(6-bromohexyl)phthalimide (1.24 g, 4.0 mmol) in DMF (10 mL) was added K2CO3 over 2 min. The reaction was heated to 90° C. for 3 h, then stirred at r.t. overnight. The mixture was concentrated and water (10 mL) added. This was extracted with ether (3×30 mL) and the combined organics washed with pH 7 phosphate buffer (20 mL), dried with Na2SO4, and concentrated to give the title compound as a clear oil.

Workup

  1. concentrationThe mixture was concentrated
  2. additionwater (10 mL) added
  3. extractionThis was extracted with ether (3×30 mL)
  4. washthe combined organics washed with pH 7 phosphate buffer (20 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ff0255827d494183b7b401b62cfe608f
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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