Reacción #361232

Ecuación de reacción

hydrogen chloride

(S)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine

benzaldehyde

hydrogen

→

(S)-N-benzyl-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine hydrochloride

Disolventes

ethyl acetate

ethyl acetate

ethanol

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for an additional 1.5 hours
3. 3
   FiltraciónThe catalyst was filtered off
4. 4
   Lavadowashed with ethanol
5. 5
   OtroRemoval of the solvent in vacuo
6. 6
   Otrogave the residue, which
7. 7
   workup.ADDITIONTo this solution was added
8. 8
   workup.STIRRINGwith mechanically stirring in an ice-bath
9. 9
   workup.STIRRINGAfter stirring at ambient temperature for 1.5 hours
10. 10
    Filtraciónthe mixture was filtered
11. 11
    Lavadothe cake was washed with ethyl acetate (50 ml)
12. 12
    OtroThe product was dried in vacuo

Procedimiento

(S)-3-Methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine hydrochloride (35.5 g) was neutralized with cold 2N sodium hydroxide (155 ml) and the mixture was extracted once with ethyl acetate (310 ml). The extract was washed once with brine (155 ml), dried over anhydrous sodium sulfate, and concentrated in vacuo to afford (S)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (30.1 g). A mixture of (S)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (30.1 g), 10% palladium on carbon (50% wet; 5.96 g), acetic acid (0.89 ml), benzaldehyde (31.6 ml), and ethanol (300 ml) was stirred at ambient temperature for 3 hours. Then, hydrogen was introduced to the mixture and stirring was continued for an additional 1.5 hours. The catalyst was filtered off and washed with ethanol. Removal of the solvent in vacuo gave the residue, which was dissolved in ethyl acetate (423 ml). To this solution was added, with mechanically stirring in an ice-bath, 4N hydrogen chloride in ethyl acetate (77 ml). After stirring at ambient temperature for 1.5 hours, the mixture was filtered and the cake was washed with ethyl acetate (50 ml). The product was dried in vacuo to give (S)-N-benzyl-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine hydrochloride (47.3 g) as a white solid.

Fuente