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Bencyclane

Bencyclane
Structural formula of bencyclane
Ball-and-stick model of the bencyclane molecule
Names
IUPAC name
3-[(1-benzylcycloheptyl)oxy]-N,N-dimethylpropan-1-amine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.016.861 Edit this at Wikidata
UNII
  • InChI=1S/C19H31NO/c1-20(2)15-10-16-21-19(13-8-3-4-9-14-19)17-18-11-6-5-7-12-18/h5-7,11-12H,3-4,8-10,13-17H2,1-2H3 checkY
    Key: FYJJXENSONZJRG-UHFFFAOYSA-N checkY
  • InChI=1/C19H31NO/c1-20(2)15-10-16-21-19(13-8-3-4-9-14-19)17-18-11-6-5-7-12-18/h5-7,11-12H,3-4,8-10,13-17H2,1-2H3
    Key: FYJJXENSONZJRG-UHFFFAOYAM
  • O(CCCN(C)C)C1(CCCCCC1)Cc2ccccc2
Properties
C19H31NO
Molar mass 289.45554
Pharmacology
C04AX11 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Bencyclane is an antispasmodic, vasodilator, and platelet aggregation inhibitor.[1]

Synthesis

Synthesis:[2][3] Patents:[4][5]

Grignard addition of benzylmagnesiumbromide to suberone would give 1-benzylcycloheptanol [4006-73-9] (1'). Williamson ether synthesis with 3-dimethylaminopropylchloride [109-54-6] (2) completed the synthesis of bencyclane (3).

See also

References

  1. ^ J. Elks, ed. (2014). The Dictionary of Drugs: Chemical Data, Structures and Bibliographies. Springer.
  2. ^ Pallos, L.; Budai, Z.; Zólyomi, G. (1972). "Basic ethers of 1-substituted cycloalkanols. 1". Arzneimittel-Forschung. 22 (9): 1502–1505. PMID 4678613.
  3. ^ Pallos, L.; Budai, Z.; Zólyomi, G. (1972). "Basic ethers of 1-substituted cycloalkanols. 2". Arzneimittel-Forschung. 22 (9): 1505–1509. PMID 4678614.
  4. ^ Anon., ES 376120  (1972-04-01 to Gallardo Antonio SA).
  5. ^ Spaeter Genannt Werden Wird, DE 2455051A1  (1975 to Andreu S A Lab).


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