ChemicalBook CAS DataBase List 2,3,4,5-Tetrahydro-1H-benzo[b]azepine

2,3,4,5-Tetrahydro-1H-benzo[b]azepine synthesis

12synthesis methods

Product Name:2,3,4,5-Tetrahydro-1H-benzo[b]azepine
CAS Number:1701-57-1
Molecular formula:C10H13N
Molecular Weight:147.22

1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

4424-80-0
141 suppliers
$25.00/1g

1701-57-1
130 suppliers
$9.00/100mg

Yield: 98%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran

Steps:

B Step B
Step B A solution of 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (2.71 g, 16.7 mmol) in THF (40 mL) was added dropwise to a suspension of LAH (1.27 g, 33.4 mmol) in ether (150 mL) at room temperature. The mixture was refluxed for 16 h. Saturated Rochelle's salt solution (15 mL) was added to the mixture cooled with an ice-water bath. The mixture was stirred for 2 hrs and the two layers were separated. The aqueous layer was extracted with ether (2*25 mL). The combined organic layer was dried (Na₂SO₄), concentrated in vacuo and flash column chromatography (EtOAc:hexane/3:7) gave 2,3,4,5-tetrahydro-1H-1-benzazepine (2.40 g, 98%) as a yellow liquid. ¹H NMR (CDCl₃, 300 MHz) δ1.58-1.70 (m, 2H), 1.72-1.86 (m, 2H), 2.72-2.82 (m, 2H), 3.00-3.10 (m, 2H), 3.78 (br, 1H), 6.74 (dd, J=1.1, 7.7 Hz, 1H), 6.82 (td, J=7.3, 1.1 Hz, 1H), 7.04 (td, J=7.5, 1.5 Hz, 1H), 7.11 (d, J=7.4 Hz, 1H) ppm.

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