ChemicalBook CAS DataBase List (S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride

(S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride synthesis

10synthesis methods

Product Name:(S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride
CAS Number:93601-86-6
Molecular formula:C14H22ClNO
Molecular Weight:255.79

1352917-67-9
1 suppliers
inquiry

(S)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine hydrochloride

93601-86-6
89 suppliers
$140.00/50mg

Yield: 84%

Reaction Conditions:

Stage #1:(S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (S)-2-hydroxy-3-phenylpropionate with sodium hydroxide in 2-methyltetrahydrofuran;water at 20;
Stage #2: with hydrogenchloride in 2-methyltetrahydrofuran;water at 60;

Steps:

5.a
Example 5a. Preparation of substantially optically pure ((S)-1 ,2,3,4-tetrahydro-5- methoxy-N-propyl- naphthalen-2-ammonium hydrochloride (la) from salt (Vac); The isolated diastereomeric salt (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl- naphthalen-2-ammonium (S)-2-hydroxy-3-phenylpropionate (Vac) was suspended into a mixture of Me-THF (5 vol) and water (2 vol). Sodium hydroxide (1.1 eq) was added as a solid. The resulting suspension was stirred at room temperature until complete solubilisation. The layers were let to settle and the aqueous layer was discarded. The organic layer was washed twice with deionised water (2 vol), then heated at 60°C. (la) was formed by addition of a 37% solution of hydrochloric acid (1.1 eq.). After cooling at 0-10°C, the resulting solid was filtered, washed twice with Me-THF and dried under vacuum to afford (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl- naphthalen-2-amine hydrochloride (la) in (yield : 84%.; chiral HPLC : 100 % of (la)).NMR 1H (dmso

References:

UCB PHARMA GMBH;ATES, Célal;SCHULE, Arnaud;PALACIO, Magali;DEUTSCH, Paul;VASSELIN, David;CARLY, Nicolas;PHADTARE, Ganesh;YERANDE, Swapnil;DELATINNE, Jean-Pierre;ESCUDERO HERNANDEZ, Maria Luisa;PINILLA, Véronique WO2011/161255, 2011, A2 Location in patent:Page/Page column 31

(S)-5-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine (R)-2-(2-chlorophenyl)-2-hydroxyacetate

1352917-66-8
0 suppliers
inquiry

93601-86-6
89 suppliers
$140.00/50mg

References

(S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-naphthalen-2-ammonium (S)-2-methoxy-2-phenylacetate

1352917-68-0
1 suppliers
inquiry

93601-86-6
89 suppliers
$140.00/50mg

References

(S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-Naphthalenamine(Rotigotine)

101403-24-1
40 suppliers
inquiry

93601-86-6
89 suppliers
$140.00/50mg

References

1256261-00-3
1 suppliers
inquiry

93601-86-6
89 suppliers
$140.00/50mg

References