6-Morpholino-3,4-dihydronaphthalen-1(2H)-one synthesis
- Product Name:6-Morpholino-3,4-dihydronaphthalen-1(2H)-one
- CAS Number:15300-12-6
- Molecular formula:C14H17NO2
- Molecular Weight:231.29
Yield:15300-12-6 31%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 60;Inert atmosphere;
Steps:
16.TP44 TP44
To 1.00 g of 6-amino-3,4-dihydronaphthalen-l(2H)-one (6.20 mmol) dissolved in 6.2 mL of DMF was added 2.57 g of K2CO3 and 0.78 mL of (2- bromoethyl)ether (6.20 mmol). The reaction was placed under argon and stirred at 60 °C overnight. The reaction was cooled, diluted with water, and rinsed with EtOAc. The combined organic layers were washed with water, brine, dried, and concentrated to give an orange oil which was chromatographed with 0-45% EtOAc in hexane to yield 0.44 g of product (31%). XH NMR (300 MHz, CDC13) δ 7.96 (d, J= 8.9, 1H), 6.79 (dd, J= 2.6, 8.9, 1H), 6.61 (d, J= 2.4, 1H), 3.89 - 3.81 (m, 4H), 3.36 - 3.27 (m, 4H), 2.89 (t, J= 6.1, 2H), 2.64 - 2.53 (m, 2H), 2.17 - 2.06 (m, 2H), MS 232 (M +1).
References:
WO2014/164704,2014,A2 Location in patent:Page/Page column 89
