Hydrogen Bromide → (6S)-6-(Propylamino)-5,6,7,8-tetrahydronaphthalen-1-ol--hydrogen bromide (1/1)
Reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C@H:7]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:8]2.Cl.[BrH:18]>>[BrH:18].[CH2:14]([NH:13][C@H:7]1[CH2:6][CH2:5][C:4]2[C:3]([OH:2])=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8]1)[CH2:15][CH3:16]Participants
4
Procedure
A mixture of (S)-1,2,3,4-tetrahydro-5-methoxy-N-propyl-2-naphthalenamine (10.0 g, 0.0391 mol) as the HCl salt, or its corresponding free base, was heated at reflux in 48% hydrobromic acid (150 mL) for a period of two to three hours. The solution was cooled to room temperature and the resulting solid was collected by filtration. Drying under high vacuum at 60° C. gave 10.7 g of the product (96% yield).