Dibenz[b,e]oxepin-11(6H)-one

Pale Yellow Solid

3-(N, N-dimethylamino)propylmagnesium chloride was prepared from magnesium turnings(0.04 mol) activated with iodine at 75 C for 1 h. THF (1 mL), toluene (4 mL) and some drops of methyl iodide was added at 65 C and stirred for 30 min. 3-chloro-N, N-dimethylpropylamine(0.03 mol) in toluene (15 mL) was added slowly. After 30 min 1a (0.02mol) in 10 mL toluene was added. The reaction mixture was stirred vigorously at 65 C for 2h. Concentrated hydrochloric acid (20 mL) was added slowly (30 min) and the reaction mixture stirred for 1 h. The organic phase was separated and the aqueous phase extracted with~ S16 ~diethyl ether (200 mL). The aqueous phase was made alkaline with aqueous ammonia and extracted with diethyl ether. The organic phase was dried over anhydrous Na2SO4, filtered and the diethyl ether was removed under reduced pressure to give 0.19 g (0.7 mmol, 70%) of 3 as a colourless oil. The 1H NMR spectrum of the reaction crude product showed it to consist of a mixture the expected geometric E- (80%) and Z- (20%) isomers in different proportions. The majority (E)-diastereoisomer was easily separated by crystallisation of the corresponding maleate. 1.H NMR (CDCl3, 300 MHz) 2.60-2.74 (m, 4H), 2.70 (s, 6H), 4.80 (brs, 1H), 5.50 (brs, 1H), 14 5.91 (t, J = 7.0 Hz, 1H), 6.75-7.40 (m, 8H); 13C NMR (CDCl3, 75 MHz) 24.9, 42.4, 60.2, 73.7, 119.2, 121.2, 127.5, 127.9, 128.2, 128.3, 128.5, 128.8, 129.4, 130.3, 134.4, 141.1, 141.3, 155.2. MS m/z: 279 (40), 219 (22), 282 (25), 189 (30), 178 (40), 165 (45), 115 (25), 59 (50), 58 (100). IR (KBr) nu [cm-1] = 3050, 3025, 1698, 1582, 1483, 1431. HRMS (EI) m/z = 279.1623 calcd for C19H21NO, found 279.1628.

Doxepin intermediate. A photodecomposition product of Doxepin.

Molecular Weight:210.23
XLogP3:2.9
Hydrogen Bond Acceptor Count:2
Exact Mass:210.068079557
Monoisotopic Mass:210.068079557
Topological Polar Surface Area:26.3
Heavy Atom Count:16
Complexity:274
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes