Water → (7-Dipropylamino-5,6,7,8-tetrahydro-naphthalen-1-yl)-methanol

Alternatively,a solution of 2-dipropylamino-8-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene (480 mg, 1.66 mMol) in tetrahydrofuran (5 mL) was added dropwise to a suspension of lithium aluminum hydride (100 mg, 2.49 mMol) in tetrahydrofuran (10 mL), and the reaction mixture was stirred at room temperature for 2.5 hours. The reaction mixture was then cooled to 0° C., and to it were added sequentially water (0.1 mL), 15% aqueous sodium hydroxide (0.1 mL) and water (0.3 mL). The suspension was then stirred at room temperature for one-half hour and was then filtered through a bed of Celite. The filtrate was concentrated in vacuo to give the title compound as a colorless, viscous oil (400 mg, 92%). The hydrochloride salt was formed and recrystallized (ethanol/diethyl ether) to give colorless crystals (m.p.=142° C.). Analysis: Calculated for C17H27NO·HCl: Theory: C, 69.02, H, 8.86, N, 4.73; Found: C, 69.03, H, 8.72, N, 4.61.

1. temperatureThe reaction mixture was then cooled to 0° C.
2. stirringThe suspension was then stirred at room temperature for one-half hour
3. filtrationwas then filtered through a bed of Celite
4. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-67a6abff10f5454d9ae3aa4feabdb58b

Source dataset

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05389687