| Identification | Back Directory | [Name]
2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine | [CAS]
132813-14-0 | [Synonyms]
132813-14-0
BlonserinImpurity14
Blonanserin Impurity 14
Blonanserin Intermediate
2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10...
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[...
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocyclooctapyridine
2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine
Cycloocta[b]pyridine, 2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydro- | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C17H17ClFN | [MDL Number]
MFCD09955376 | [MOL File]
132813-14-0.mol | [Molecular Weight]
289.77 |
| Chemical Properties | Back Directory | [Melting point ]
137-140°C | [Boiling point ]
414.7±45.0 °C(Predicted) | [density ]
1.175 | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
1.49±0.20(Predicted) | [color ]
Off-White |
| Hazard Information | Back Directory | [Uses]
2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine is an intermediate in the synthesis of Blonanserin (B595850), a 5-HT2 serotonin receptor and D2 dopamine receptor antagonist, used as an antipsychotic. | [Synthesis]
General procedure for the synthesis of 2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine from 4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine as 4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine: 80.0 g of 4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b] Pyridin-2(1H)-one was dissolved in 520 mL of dimethylformamide and cooled to 5 °C. Under stirring, 36.84 g of phosphorus pentachloride was added in 10 portions. After addition, the temperature of the reaction system was raised to 15 °C and the reaction was continued for 3 hours. Upon completion of the reaction, 520 mL of purified water was added to the reaction mixture and stirred at 10 °C for 1 hour. The reaction solution was filtered using a Brinell funnel (Coors), the precipitated crystals were collected and the filter cake was washed with 300 mL of purified water. The resulting crystals were dried at 70 °C to afford 80.0 g of off-white 2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine in 93.6% yield. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 4, p. 1055 - 1059
[2] Patent: KR2015/117123, 2015, A. Location in patent: Paragraph 0046; 0047; 0048
[3] Patent: , 2016, . Location in patent: Paragraph 0026; 0027; 0028; 0029
[4] Asian Journal of Chemistry, 2014, vol. 26, # 18, p. 5928 - 5930
[5] Patent: JP2018/43989, 2018, A. Location in patent: Paragraph 0136-0138 |
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