[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1.[Br:12][CH2:13][CH2:14][CH2:15][OH:16].C(O)CCC.O.C(O)(=O)C>O1CCOCC1.CCOCC>[Br-:12].[OH:16][CH2:15][CH2:14][CH2:13][N+:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1A solution of lepidine (0.49 g, 3.43 mmol) and 3-bromo-1-propanol (3.1 ml, 34 mmol) in 3.0 ml of 1,4-dioxane was refluxed for 17 h. The solution was cooled to room temperature and then diluted with 30 ml of ether. The product separated as an oil and the ether layer was discarded. The oil was crystallized from methylene chloride: 367-mg (38%) yield; TLC (5:3:2, n-butanol/water/acetic acid), Rf=0.40; 1H NMR δ 9.39 (1H, d, J=6.0 Hz, aromatic), 8.57 (2H, t, J=9.1 Hz, aromatic), 8.27 (1H, t, J=7.8 Hz, aromatic), 8.05 (2H, m, aromatic), 5.08 (2H, t, J=7.1 Hz, methylene), 4.81 (1H, t, J=4.9 Hz, hydroxyl), 3.51 (2H, m, methylene), 3.01 (3H, s, 4-methyl), 2.11 (2H, m, methylene). Anal. Calcd. For C13H16BrNO 0.3H2O; C, 54.29; H, 5.82; N, 4.87. Found C, 53.92; H, 5.43; N, 4.67.
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