1-Chloro-4-(chloromethyl)benzene → HCID 22850905, compound

Participants

Reaction Steps

Following the procedure of Example 3, step 4, 0.202 g (1.08 mmol) of crude trans-1,2,3,4,4a,5,6,10b-octahydro benz[f]isoquinoline in 10 ml of anhydrous DMF was reacted with 0.164 g (1.19 mmol) of anhydrous potassium carbonate and 0.183 g (1.14 mmol) of 4-chlorobenzyl chloride. Chromatography on flash silica, eluting with 30% ethyl acetate/petroleum ether, gave 0.110 g (33%) of the title product as a white solid. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent the title product hydrochloride was obtained as a white solid, m.p. 257°-259° C. NMR δ(D2O/CD3CN) 1.51 (1H, m), 1.65 (1H, m), 1.78-1.82 (2H, m), 2.59-2.67 (2H, m), 2.80-2.89 (3H, m), 3.13 (1H, t of d), 3.41 (1H, m), 3.60 (1H, m), 4.29 (2H, d, J=3.7 Hz), 7.14-7.20 (3H, m), 7.25-7.28 (1H, m), 7.52 (4H, m). m/z (CI+, NH3) 312 (M+H)+, 186 (M-CH2C6H4Cl) +, 125. Analysis calcd. for C20H23Cl2N: C, 68.97; H, 6.66; N, 4.02%. Found: C, 68.59; H, 6.63; N, 3.98%.

Provenance & Evidence