4'-Hydroxyacetophenone → 1-(4-[3-(Diethylamino)propoxy]phenyl)ethanone
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S([O-])(=O)(=O)C.[CH2:22]([N:24]([CH:27](O)[CH2:28][CH3:29])[CH2:25][CH3:26])[CH3:23].CS(Cl)(=O)=O>CN(C=O)C.O.CCOC(C)=O>[CH2:22]([N:24]([CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH3:23]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 4′-hydroxyacetophenone (2.2 mmol) in DMF (10 mL) at rt, solid potassium carbonate (8.0 mmol) was added. The mesylate of N,N-diethyaminopropanol (prepared from the corresponding alcohol and methanesulfonyl chloride) (2.0 mmol) was added to the reaction mixture and heated to 80° C. until completion according to General Procedure Q1, as indicated by TLC or HPLC. After cooling to rt, the reaction mixture was diluted with water and the product was isolated in EtOAc. The combined organic layers were washed with saturated sodium bicarbonate (2×15 ml), water (2×15 ml) and brine (15 ml). The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuuo to afford the desired 1-{4-[3-(diethylamino)propoxy]phenyl}ethanone. The crude alkylated product was purified using silica gel column chromatography. Pure product was obtained with 2–3% MeOH/DCM. (yield 50–60%)
Workup
- additionwas added to the reaction mixture
- temperatureAfter cooling to rt
- washThe combined organic layers were washed with saturated sodium bicarbonate (2×15 ml), water (2×15 ml) and brine (15 ml)
- dry with materialThe organic layer was dried over magnesium sulfate
- customthe solvent was removed in vacuuo
Sources & evidence
- ORD record
- ord-788a5ea6bd5640c2afd3c09ea4fb19c5
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07361678B2
Reaction notes
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