7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one Chemical Properties

Melting point:

244.0 to 248.0 °C

Boiling point:

455.8±45.0 °C(Predicted)

Density 

1.167

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

Solid

pka

13.29±0.20(Predicted)

color 

Off-White to Pale Beige

InChI

InChI=1S/C12H13NO3/c1-15-10-5-8-3-4-13-12(14)7-9(8)6-11(10)16-2/h3-6H,7H2,1-2H3,(H,13,14)

InChIKey

CPNZASIAJKSBBH-UHFFFAOYSA-N

SMILES

N1C=CC2=CC(OC)=C(OC)C=C2CC1=O

LogP

1.23 at 23℃ and pH6.47

Surface tension

71mN/m at 36.9mg/L and 19℃

CAS DataBase Reference

73942-87-7(CAS DataBase Reference)

Safety Information

HS Code 

2914390090

7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one Usage And Synthesis

Uses

7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is a substituted benzazepinonee derivative used in the preparation of bradycardic agents as well as isoform-selective f-current blockers.

Application

7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is used in the industrial preparation of pharmaceuticals and can be reacted with trifluoroacetic acid to form 3,4-dimethoxyphenylacetic acid.

Definition

ChEBI: 7,8-dimethoxy-1,3-dihydro-3-benzazepin-2-one is a benzazepine.

Synthesis

1.Charge 142.0 g of N-(2,2-dimethoxyethyl)-2-(3,4-dimethoxyphenyl) acetamide, 710 ml of glacial acetic acid and 710 ml of conc. hydrochloric acid in a 3.0 L round bottom flask equipped with mechanical stirrer and thermometer pocket at 25°C.
2.Stir the mixture for 17 hours at 25°C.
3.Monitor the reaction by HPLC (starting material should be less than 4.0%).
4.Pour the reaction mixture on 3.0 kg of crushed ice, if HPLC complies.
5.Stir the mixture for 30 minutes and filter the solid material.
6.Wash the mixture with 1 L of water, suck dry and unload the material.
7.Dry the 7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one under vacuum at 55-60°C till the LOD comes to below 0.5%.

References

[1] Patent: WO2010/72409, 2010, A1. Location in patent: Page/Page column 17-18
[2] Journal of Medicinal Chemistry, 1990, vol. 33, # 5, p. 1496 - 1504
[3] Patent: CN104031042, 2017, B. Location in patent: Paragraph 0109; 0110
[4] Patent: US4584293, 1986, A
[5] Patent: US4604389, 1986, A

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