N,N-Dimethylaniline → HCID 10269744, compound

Participants

Reaction Steps

8-Chloro-10H-dibenzo[b,f][1,4]thiazepin-11-one 2 (X=S and R1=Cl) (0.5 g, 1.91 mol), phosphorus oxychloride (5 ml, 53 mmol), toluene (25 ml) and N,N-dimethylaniline (1.0 ml) were heated at reflux for 3 hours. After evaporation of the volatiles, 25 ml of toluene and 5 ml (45 mmol) of 1-ethylpiperazine were added. Work-up and purification as described in Example 1 gave 150 mg (22%) of light yellow crystals, mp 100-101° C., 1H NMR (300 MHz, CDCl3), 1.11 (t, 3H, J=6.0 Hz, CH3), 2.55 (q, 2H, J=6.0 Hz, —CH2—), 2.55-2.65 (broad s, 4H, piperazinyl CH2), 3.55-3.65 (broad s, 4H, piperazinyl CH2), 6.83 (dd, 1H, J=1.5 and 6.0 Hz), 7.07 (d, 1H, J=1.5 Hz), 7.25-7.40 (mult., 4H), 7.50 (dd, 1H, J=7.5 Hz), MS (EI) m/z 357 (M+, 16.1%), 244(34.2), 209(30.1), 97(93.7), 84(100), HRMS calcd for C19H20N3SCl 357.1066, found 357.1067.

Provenance & Evidence