1-(1-Naphthyl)ethylamine → (R)-N-[3-(2-chlorophenyl)propyl]-1-(1-naphthyl)ethylamine

A stirred solution of 2-chlorohydrocinnamonitrile (Aldrich Chemical Co., 1.66 g, 10 mmol) in dichloromethane (100 ml) was cooled to −78° C. and treated dropwise with diisobutylaluminum hydride (1.42 g, 10 mmol). The reaction was stirred 1 hr at rt, cooled to −78° C. and treated with a solution of 1-(1-naphthyl)ethylamine (1.71 g, 10 mmol) in dichloromethane (25 ml). The reaction was transferred to an ice bath and stirred 2 hr. After this time the reaction was poured directly into a stirred solution of ethanolic sodium borohydride (50 ml of 0.2 M, 10 mmol). The mixture was stirred 30 min at rt and the excess sodium borohydride quenched by the addition of 10% HCl. The solution was then made basic by the addition of 10 N NaOH and transferred to a separatory funnel washing with diethyl ether (300 ml). The aqueous phase was removed and the remaining organic layer washed with 1 N NaOH (3×100 ml). The organic layer was dried over anhydrous magnesium sulfate, and concentrated to an oil. Chromatography of this material through silica gel using a gradient of chloroform to 10% methanol-chloroform afforded 2.34 g (72% yield) of (R)-N-[3-(2-chlorophenyl)propyl]-1-(1-naphthyl)ethylamine, 12Z, as a clear oil; m/z (rel. int.) 323 (M+, 2), 308 (63), 288 (7), 196 (5), 184 (5), 155 (100), 125 (24), 115 (8), 103 (4), 91 (3), 77 (7).

1. temperaturecooled to −78° C.
2. customThe reaction was transferred to an ice bath
3. stirringstirred 2 hr
4. stirringThe mixture was stirred 30 min at rt
5. customthe excess sodium borohydride quenched by the addition of 10% HCl
6. additionThe solution was then made basic by the addition of 10 N NaOH
7. customtransferred to a separatory funnel
8. washwashing with diethyl ether (300 ml)
9. customThe aqueous phase was removed
10. washthe remaining organic layer washed with 1 N NaOH (3×100 ml)
11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
12. concentrationconcentrated to an oil

ORDレコード

ord-2ba5d45a48664d84bd244c7c7d429d29

出典データセット

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06211244B1