(S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine synthesis
- Product Name:(S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine
- CAS Number:1148154-91-9
- Molecular formula:C20H27NOS
- Molecular Weight:329.5
![2-Thiopheneethanamine, N-[(2S)-1,2,3,4-tetrahydro-5-methoxy-2-naphthalenyl]-](/CAS/20200611/GIF/1232344-40-9.gif)
Yield:1148154-91-9 95%
Reaction Conditions:
with sodium hydrogencarbonate in N,N-dimethyl-formamide at 20 - 85;Inert atmosphere;
Steps:
6
Example 6 Preparation of (S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl-)ethyl)-tetralin-2-amine (Compound 4) A 250 mL three-necked reaction flask was equipped with a mechanical agitator, a thermometer and a condenser, and protected under nitrogen from the top of the condenser. The S-5-methoxy-N-2'-(thien-2-yl-)ethyl-tetralin-2-amine (10g, 34.8mmol) prepared above in Example 5, iodopropane (11.83g, 69.6mmol), NaHCO3 (5.8g, 69.6mmol) and DMF (50mL) were added thereto at room temperature, and heated to 85°C to react overnight. After cooling to room temperature, 100mL ethyl acetate and 100mL water were added, and the mixture was left alone and partitioned. The organic phases were washed with a saturated aqueous sodium chloride solution twice and concentrated to give a crude oily (S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl-)ethyl)-tetralin-2-amine with a purity of 96% and a yield of 95%, which may be directly used for the next step without further purification.
References:
EP2476676,2012,A1 Location in patent:Page/Page column 7-8
