2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine supplier

Name
2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine
EINECS 1592732-453-0
CAS No. 132813-14-0
Article Data7
CAS DataBase
Density 1.175 g/cm³
Solubility
Melting Point
Formula C₁₇H₁₇ClFN
Boiling Point 414.7 °C at 760 mmHg
Molecular Weight 289.78
Flash Point 204.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine;
PSA 12.89000
LogP 5.20010

Synthetic route

: 132812-72-7
4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocyclooctane[b]pyridine-(1H)-ketone

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Conditions

Conditions	Yield
With trichlorophosphate	95%
With phosphorus pentachloride In N,N-dimethyl-formamide at 5 - 15℃; for 3h;	93.6%
With hydrogenchloride In water; acetic anhydride at 10 - 20℃; for 6h; Cooling with ice; Green chemistry;	93.24%

: 502-49-8
cycloactanone

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / PPA / Heating 2: 95 percent / POCl3 View Scheme
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; phosphoric acid / toluene / Reflux; Dean-Stark; Large scale 2: P,P-dichlorophenylphosphine oxide / toluene; dichloromethane / 80 - 148 °C / Large scale View Scheme

: 4640-67-9
3-(4-fluorophenyl)-3-oxopropionitrile

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / PPA / Heating 2: 95 percent / POCl3 View Scheme
Multi-step reaction with 3 steps 1: methanesulfonic acid / water / 3 h / 65 - 70 °C 2: methanesulfonic acid / water / 2 h / 110 - 115 °C 3: Dichlorophenylphosphine / 4 h / 155 - 160 °C View Scheme
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; phosphoric acid / toluene / Reflux; Dean-Stark; Large scale 2: P,P-dichlorophenylphosphine oxide / toluene; dichloromethane / 80 - 148 °C / Large scale View Scheme

: 3-(4-fluorophenyl)-3-oxopropanamide

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanesulfonic acid / water / 2 h / 110 - 115 °C 2: Dichlorophenylphosphine / 4 h / 155 - 160 °C View Scheme

: 403-33-8
methyl 4-flurobenzoate

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hexamethyldisilazane / toluene; tetrahydrofuran / -5 - 0 °C / Large scale 2: toluene-4-sulfonic acid; phosphoric acid / toluene / Reflux; Dean-Stark; Large scale 3: P,P-dichlorophenylphosphine oxide / toluene; dichloromethane / 80 - 148 °C / Large scale View Scheme
Multi-step reaction with 3 steps 1: sodium hydride / tert-butyl methyl ether; water / 90 °C 2: toluene-4-sulfonic acid; phosphoric acid / toluene / Reflux; Dean-Stark; Large scale 3: P,P-dichlorophenylphosphine oxide / toluene; dichloromethane / 80 - 148 °C / Large scale View Scheme

: 5308-25-8
4-ethylpiperazine

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: blonanserin

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 5h;	98.6%
Stage #1: 4-ethylpiperazine; 2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine With sodium t-butanolate In toluene at 10℃; under 75.0075 Torr; for 0.0333333h; Inert atmosphere; Stage #2: With palladium diacetate; triphenylphosphine In toluene at 70℃; under 75.0075 Torr; for 7h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	89.12%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 75 - 85℃; for 3h; Large scale;	88%

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: 143213-96-1
2-chloro-4-(4-fluoro-phenyl)-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridine 1-oxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform	97%

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: 2-(piperazine-1-yl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Conditions

Conditions	Yield
Stage #1: 1-t-Butoxycarbonylpiperazine; 2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine With potassium iodide In N,N-dimethyl-formamide for 12h; Reflux; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 30℃; for 2h; Temperature; Solvent; Reagent/catalyst;	80%

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: 2-chloro-4-(4-fluoro-phenyl)-5,6,7,8-tetrahydro-cycloocta[b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / m-CPBA / CHCl3 2: 97 percent / POCl3; Et3N / CHCl3 3: 84 percent / DBU / dimethylsulfoxide View Scheme

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: 848301-81-5
2-chloro-4-(4-fluoro-phenyl)-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridin-8-ol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 97 percent / m-CPBA / CHCl3 2: 97 percent / POCl3; Et3N / CHCl3 3: 84 percent / DBU / dimethylsulfoxide 4: 99 percent / SeO2 / dioxane 5: 49 percent / HCl / methanol 6: 85 percent / H2 / PtO2 / ethanol View Scheme

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: 2-chloro-4-(4-fluoro-phenyl)-5,6,7,8-tetrahydro-cycloocta[b]pyridin-8-ol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 97 percent / m-CPBA / CHCl3 2: 97 percent / POCl3; Et3N / CHCl3 3: 84 percent / DBU / dimethylsulfoxide 4: 99 percent / SeO2 / dioxane 5: 49 percent / HCl / methanol View Scheme

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: 143213-95-0
2,10-dichloro-4-(4-fluoro-phenyl)-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / m-CPBA / CHCl3 2: 97 percent / POCl3; Et3N / CHCl3 View Scheme

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: formic acid 2-chloro-4-(4-fluoro-phenyl)-5,6,7,8-tetrahydro-cycloocta[b]pyridin-8-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 97 percent / m-CPBA / CHCl3 2: 97 percent / POCl3; Et3N / CHCl3 3: 84 percent / DBU / dimethylsulfoxide 4: 99 percent / SeO2 / dioxane View Scheme

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: 848301-82-6
2-(4-ethyl-piperazin-1-yl)-4-(4-fluoro-phenyl)-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridin-8-ol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 97 percent / m-CPBA / CHCl3 2: 97 percent / POCl3; Et3N / CHCl3 3: 84 percent / DBU / dimethylsulfoxide 4: 99 percent / SeO2 / dioxane 5: 49 percent / HCl / methanol 6: 85 percent / H2 / PtO2 / ethanol View Scheme

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: 2-(4-ethyl-piperazin-1-yl)-4-(4-fluoro-phenyl)-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridin-8-ol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 97 percent / m-CPBA / CHCl3 2: 97 percent / POCl3; Et3N / CHCl3 3: 84 percent / DBU / dimethylsulfoxide 4: 99 percent / SeO2 / dioxane 5: 49 percent / HCl / methanol 6: 85 percent / H2 / PtO2 / ethanol 7: resolution using CHIRACEL OJ column View Scheme

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: 2-(4-ethyl-piperazin-1-yl)-4-(4-fluoro-phenyl)-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridin-8-ol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 97 percent / m-CPBA / CHCl3 2: 97 percent / POCl3; Et3N / CHCl3 3: 84 percent / DBU / dimethylsulfoxide 4: 99 percent / SeO2 / dioxane 5: 49 percent / HCl / methanol 6: 85 percent / H2 / PtO2 / ethanol 7: resolution using CHIRACEL OJ column View Scheme

: 110-85-0
piperazine

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: 2-(piperazine-1-yl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Conditions

Conditions	Yield
With potassium iodide at 165 - 170℃; for 8h;	8.5 g

: 5308-25-8
4-ethylpiperazine

: 132813-14-0
2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

: blonanserin sulfate

Conditions

Conditions	Yield
Stage #1: 4-ethylpiperazine; 2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine With sodium t-butanolate In toluene at 10℃; under 75.0075 Torr; for 0.0333333h; Inert atmosphere; Stage #2: With palladium diacetate; triphenylphosphine In toluene at 70℃; under 75.0075 Torr; for 7h; Inert atmosphere; Stage #3: With sulfuric acid In ethanol; toluene at 0 - 10℃; for 0.5h; Inert atmosphere;	6.76 g

Yield

Stage #1: 4-ethylpiperazine; 2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine With sodium t-butanolate In toluene at 10℃; under 75.0075 Torr; for 0.0333333h; Inert atmosphere;
Stage #2: With palladium diacetate; triphenylphosphine In toluene at 70℃; under 75.0075 Torr; for 7h; Inert atmosphere;
Stage #3: With sulfuric acid In ethanol; toluene at 0 - 10℃; for 0.5h; Inert atmosphere;

6.76 g

2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine Specification

The systematic name of this chemical is 2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine. With the CAS registry number 132813-14-0, it is also named as Cycloocta[b]pyridine,2-chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydro-. In addition, the formula is C₁₇H₁₇ClFN and the molecular weight is 289.77.

The other characteristics of 2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine can be summarized as: (1)ACD/LogP: 5.98; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.98; (4)ACD/LogD (pH 7.4): 5.98; (5)ACD/BCF (pH 5.5): 20638.1; (6)ACD/BCF (pH 7.4): 20639.25; (7)ACD/KOC (pH 5.5): 42659.88; (8)ACD/KOC (pH 7.4): 42662.27; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 12.89 Å²; (13)Index of Refraction: 1.561; (14)Molar Refractivity: 79.83 cm³; (15)Molar Volume: 246.4 cm3; (16)Polarizability: 31.64×10^-24 cm³; (17)Surface Tension: 41.1 dyne/cm; (18)Density: 1.175 g/cm³; (19)Flash Point: 204.6 °C; (20)Enthalpy of Vaporization: 64.18 kJ/mol; (21)Boiling Point: 414.7 °C at 760 mmHg; (22)Vapour Pressure: 1.05E-06 mmHg at 25°C.

People can use the following data to convert to the molecule structure.
1. SMILES:Fc1ccc(cc1)c2cc(Cl)nc3CCCCCCc23
2. InChI:InChI=1/C17H17ClFN/c18-17-11-15(12-7-9-13(19)10-8-12)14-5-3-1-2-4-6-16(14)20-17/h7-11H,1-6H2
3. InChIKey:PWYYKWZKLRXRSM-UHFFFAOYAB
4. Std. InChI:InChI=1S/C17H17ClFN/c18-17-11-15(12-7-9-13(19)10-8-12)14-5-3-1-2-4-6-16(14)20-17/h7-11H,1-6H2
5. Std. InChIKey:PWYYKWZKLRXRSM-UHFFFAOYSA-N

Product Name

2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine

Synthetic route

2-Chloro-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine Specification

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