p-Xylyl bromide → HCID 17978852, compound

HRID 1591806Notes

Reaction equation

HRID 1591806 reaction equation
[OH:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[C:3](=[O:6])[CH2:4][CH3:5].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]Br)=[CH:22][CH:21]=1.[OH-].[Na+]>CS(C)=O.O>[OH:1][C:2]([C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[CH:11][CH:12]=1)([C:3](=[O:6])[CH2:4][CH3:5])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7721p-Xylyl bromideHCID 14798Sodium HydroxideHCID 17978856HCID 17978856, compound

Product 1

HCID 17978852HCID 17978852, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

1-Hydroxy-1-(4-morpholinophenyl)-butan-2-one, one equivalent of 4-methylphenylmethyl bromide and 1.2 equivalent of sodium hydroxide are suspended in dimethyl sulfoxide and the resulting mixture is stirred at room temperature for 24 hours. The reaction mixture is diluted with the same amount of water and extracted several times with dichloromethane. The combined organic extracts are dried over sodium sulfate and evaporated to give crude 2-hydroxy-2-(4-morpholinophenyl)-1-(4-methylphenyl)-pentan-3-one as a viscous oil. The compound is purified by chromatography on silica gel (eluant: hexane/ethyl acetate 9:1). Pure 2-hydroxy-2-(4-morpholinophenyl)-1-(4-methylphenyl)-pentan-3-one is thus obtained as colorless crystals with a melting point of 160° C.

Workup

  1. extractionextracted several times with dichloromethane
  2. dry with materialThe combined organic extracts are dried over sodium sulfate
  3. customevaporated
  4. customto give crude 2-hydroxy-2-(4-morpholinophenyl)-1-(4-methylphenyl)-pentan-3-one as a viscous oil
  5. customThe compound is purified by chromatography on silica gel (eluant: hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-02e6773064db4625ae1baa1b6592b6ab
Source dataset
uspto-grants-2007_11
Patent number
US07291654B2

Reaction notes

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