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Home> Encyclopedia >Pharmaceutical Intermediates>Organic Intermediate>Cardiovascular Agents
7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one structure
7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one structure

7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one

Iupac Name:3-(3-iodopropyl)-7,8-dimethoxy-1H-3-benzazepin-2-one
CAS No.: 148870-57-9
Molecular Weight:387.2128
Modify Date.: 2022-11-24 17:30
Introduction:

A mixture of the chloride of formula (Ilia) (50.00 g; 169 mmol) and sodium iodide (32.75 g; 218 mmol) in methyl isobutyl ketone (375 ml) was heated to 117 - 118°C with stirring under an argon atmosphere. Reaction progress was monitored by HPLC. After completion, the reaction mixture was concentrated in vacuo and the residue was diluted with dichloro methane (375 ml) and water (190 ml). The organic layer was separated, washed with water (190 ml) and concentrated in vacuo. The residue was treated with methyl t- butyl ether (190 ml) and the resulting suspension was cooled to 0°C. After 1 hour of stirring at 0°C, the suspension was filtered, washed with methyl i-butyl ether (40 ml) and dried for two hour at 23°C/100 mbar to afford 60.10 g of yellowish solid (92percent yield).A mixture of 7, 8-dimethoxy-3 -[3 -chloropropyl]- 1, 3 -dihydro-2H-3 -benzazepin-2-one (40g) prepared as in Example 1, and acetone (320mL) was stirred for about 10mm and sodium iodide (20g) was added to it. The reaction mixture was stirred at about reflux temperature for about 24h. The reaction mixture was cooled to about room temperature, filtered and washed with acetone. The filtrate obtained was concentrated under reducedpressure to give a solid residue. The residue obtained was dissolved in dichioromethane (400rnL). The solution obtained was washed with aqueous sodium dithionate solution and demineralized water and was concentrated under reduce pressure. The solid obtained was recrystallized with acetone and then with acetonitrile and dried under vacuum.Yield: 44.5g (85percent); HPLC purity: > 95percent

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1. Names and Identifiers
1.1 Name
7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one
1.2 Synonyms

1,3-Dihydro-3-(3-iodopropyl)-7,8-dimethoxy-2H-3-benzazepin-2-one 2H-3-Benzazepin-2-one,1,3-dihydro-3-(3-iodopropyl)-7,8-dimethoxy- 3-(3-IODOPROPYL)-7,8-DIMETHOXY-1,3-DIHYDRO-2H-3-BENZAPINE-2-ONE 3-(3-Iodopropyl)-7,8-diMethoxy-1,3-dihydro-2H-3-benzazepin-2-one 3-(3-iodopropyl)-7,8-dimethoxy-1H-3-benzazepin-2-one 7,8-Dimethoxy-3-(3-iodopropyl) 7,8-DiMethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-on Ivabradine int

1.3 CAS No.
148870-57-9
1.4 CID
19092190
1.5 EINECS(EC#)
604-658-5
1.6 Molecular Formula
C15H18INO3 (isomer)
1.7 Inchi
InChI=1S/C15H18INO3/c1-19-13-8-11-4-7-17(6-3-5-16)15(18)10-12(11)9-14(13)20-2/h4,7-9H,3,5-6,10H2,1-2H3
1.8 InChkey
VWPSZWNLEFZFQB-UHFFFAOYSA-N
1.9 Canonical Smiles
COC1=C(C=C2C=CN(C(=O)CC2=C1)CCCI)OC
1.10 Isomers Smiles
COC1=C(C=C2C=CN(C(=O)CC2=C1)CCCI)OC
2. Properties
2.1 Density
1.513
2.1 Boiling point
504.5°C at 760 mmHg
2.1 Refractive index
1.592
2.1 Flash Point
258.9°C
2.1 Precise Quality
387.03300
2.1 PSA
38.77000
2.1 logP
2.82220
2.1 pKa
-1.23±0.20(Predicted)
2.2 StorageTemp
under inert gas (nitrogen or Argon) at 2–8 °C
3. Safety and Handling
3.1 Hazard Declaration
H413
3.1 Caution Statement
P273, P501
4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 4

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

H413 May cause long lasting harmful effects to aquatic life

Precautionary statement(s)
Prevention

P273 Avoid release to the environment.

Response

none

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. Precursor and Product
7. Computational chemical data
  • Molecular Weight: 387.2128g/mol
  • Molecular Formula: C15H18INO3
  • Compound Is Canonicalized: True
  • XLogP3-AA: 2.9
  • Exact Mass: 387.03314
  • Monoisotopic Mass: 387.03314
  • Complexity: 361
  • Rotatable Bond Count: 5
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 38.8
  • Heavy Atom Count: 20
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceByMAAAAgAAAAAAAAAAAAAAAAAAAAAwAAAABAAAAAABAAAAHgAgAAAADATDmAYyBoMABACIAiFWUAACCAAgIgAIiAEOiIgNJjKEtRuEMCIkxhGKqAeY3LLOoAABAAAQQABAAAIAACCAAAAAAAAAAA==
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