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3-(dimethylamino)-1-(naphthalen-5-yl)propan-1-one synthesis
- Product Name:3-(dimethylamino)-1-(naphthalen-5-yl)propan-1-one
- CAS Number:10320-49-7
- Molecular formula:C15H17NO
- Molecular Weight:227.3
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941-98-0
378 suppliers
$5.00/10g
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50-00-0
872 suppliers
$10.00/25g
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506-59-2
552 suppliers
$5.00/5 g
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10320-49-7
121 suppliers
$30.00/250mg
Yield: 89%
Reaction Conditions:
Stage #1:1'-naphthacetophenone;formaldehyd;N,N-dimethylammonium chloride in ethanol for 2 h;Reflux;Mannich Aminomethylation;
Stage #2: with sodium hydrogencarbonate in water
Steps:
3-(Dimethylamino)-1-(naphthalen-1-yl) propan-1-one (10a).
General procedure: In 500mL three-necked bottle, 1-(naphthalen-1-yl) ethanone (9a, 25g, 0.15mol), dimethylamine hydrochloride (15.6g, 0.19mol) and paraformaldehyde (7.2g, 0.08mol) were placed in the bottle. After the addition of 0.3mL of concentrated hydrochloric acid in 40mL of 95percent ethanol, the mixture was refluxed for 2h. Then the acetone (100mL) was added while the solution was still hot. Cooled slowly to room temperature and chilled overnight in the refrigerator. Filtered and washed with acetone (2×20mL) to afford white solid 3-(dimethylamino)-1-(naphthalen-1-yl)propan-1-one Hydrochloride (26.8g, 69percent). The solid was dissolved in water, alkalinized with saturated Sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated to get colorless oleosus product (10a, 20.5g, 89percent) which was easily decomposed but suitable for next step without further purification. Compounds 10b-10f were prepared without further purification from different commercially available substituted-ethanones in a range of 59–67percent yields.
References:
Cao, Ruiyuan;Fan, Shiyong;Li, Song;Liu, Ping;Lu, Yu;Wang, Bin;Wang, Xiaokui;Zhong, Wu [Bioorganic Chemistry,2020,vol. 102]
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5409-58-5
187 suppliers
$15.00/5g
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10320-49-7
121 suppliers
$30.00/250mg
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654655-80-8
33 suppliers
$390.00/10 mg
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654655-69-3
231 suppliers
$8.00/250mg
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10320-49-7
121 suppliers
$30.00/250mg

941-98-0
378 suppliers
$5.00/10g
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50-00-0
872 suppliers
$10.00/25g
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124-40-3
521 suppliers
$18.00/100ml
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10320-49-7
121 suppliers
$30.00/250mg
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941-98-0
378 suppliers
$5.00/10g

506-59-2
552 suppliers
$5.00/5 g
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10320-49-7
121 suppliers
$30.00/250mg