8-METHOXY-2,3,4,5-TETRAHYDRO-1H-BENZO[B]AZEPINE HYDROCHLORIDE synthesis

4synthesis methods

Product Name:8-METHOXY-2,3,4,5-TETRAHYDRO-1H-BENZO[B]AZEPINE HYDROCHLORIDE
CAS Number:17422-43-4
Molecular formula:C11H15NO
Molecular Weight:177.24

22246-83-9 Synthesis

2H-1-BENZAZEPIN-2-ONE, 1,3,4,5-TETRAHYDRO-8-METHOXY-

22246-83-9
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8-METHOXY-2,3,4,5-TETRAHYDRO-1H-BENZO[B]AZEPINE HYDROCHLORIDE

17422-43-4
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Yield:17422-43-4 89%

Reaction Conditions:

Stage #1: 8-methoxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-onewith lithium aluminium tetrahydride in tetrahydrofuran; for 4 h;Reflux;
Stage #2: with water;sodium hydroxide in tetrahydrofuran;

Steps:

65 8-methoxy-2,3,4, 5-tetrahydro-1H-1-benzazepine

Reference Example 65 8-methoxy-2,3,4, 5-tetrahydro-1 H-1-benzazepine To a suspension of lithium aluminum hydride (725 mg, 19.1 mmol) in THF (15 mL) was added dropwise a solution of 8-methoxy-1,3,4, 5-tetrahydro-2H-1-benzazepin-2-one (1.46 g, 7.63 mmol) in THF (20 mL) under ice-cooling, and the mixture was refluxed for 4 hr. The reaction mixture was treated by adding dropwise water (0.75 mL), 15% aqueous sodium hydroxide solution (0.75 mL) and water (2.25 mL). The precipitate was filtered and the obtained solid was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (1.20 g, yield 89%) as an oil. ¹H-NMR (CDCl₃) δ: 1.55 - 1.69 (2H, m), 1.72 - 1.89 (2H, m), 2.64 - 2.78 (2H, m), 2.99 - 3.12 (2H, m), 3.75 (4H, s), 6.30 (1H, d, J = 2.6 Hz), 6.38 (1H, dd, J = 8.2, 2.5 Hz), 6.99 (1H, d, J = 8.1 Hz).

References:

EP2298731,2011,A1 Location in patent:Page/Page column 62-63

20175-97-7 Synthesis