4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane at 20℃; for 0.166667h; | 99% |
With sodium hydroxide In dichloromethane | 86.6% |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon In methanol at 30℃; under 2068.65 Torr; for 4h; Inert atmosphere; Autoclave; | 94% |
3-(4-chlorophenyl)-[1,2,3]triazolo[1,5-a]pyridine
t-butyl 4-hydroxy piperidine-1-carboxylate
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Stage #1: 3-(4-chlorophenyl)-[1,2,3]triazolo[1,5-a]pyridine; t-butyl 4-hydroxy piperidine-1-carboxylate With potassium carbonate In benzene at 20℃; for 10h; UV-irradiation; Stage #2: With trifluoroacetic acid at 20℃; for 1h; | 71% |
(4-chlorophenyl)-2-pyridylmethanol
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: triethylamine / toluene / 1 h / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / 3 h / 80 °C 3: sodium hydroxide / isopropyl alcohol / 12 h / Reflux 4: 5 h / 20 °C 5: sodium hydroxide / dichloromethane / 0.17 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 h / Reflux 2: 5%-palladium/activated carbon / methanol / 4 h / 30 °C / 2068.65 Torr / Inert atmosphere; Autoclave View Scheme |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / 3 h / 80 °C 2: sodium hydroxide / isopropyl alcohol / 12 h / Reflux 3: 5 h / 20 °C 4: sodium hydroxide / dichloromethane / 0.17 h / 20 °C View Scheme |
4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine-1-carboxylic acid ethyl ester
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / isopropyl alcohol / 12 h / Reflux 2: 5 h / 20 °C 3: sodium hydroxide / dichloromethane / 0.17 h / 20 °C View Scheme | |
With isopropyl alcohol; sodium hydroxide at 88℃; for 6h; |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 5 h / 20 °C 2: sodium hydroxide / dichloromethane / 0.17 h / 20 °C View Scheme |
N-acetyl-4-hydroxypiperidine
2-(chloro(4-chlorophenyl)methyl)pyridine
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Stage #1: N-acetyl-4-hydroxypiperidine; 2-[chloro(4-chlorophenyl)methyl]pyridine at 130℃; for 5h; Large scale; Stage #2: With hydrogenchloride In water at 80℃; for 15h; Large scale; |
4-HYDROXYPIPERIDINE
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 1 h / -70 °C / Large scale 1.2: 20 °C / Large scale 2.1: 5 h / 130 °C / Large scale 2.2: 15 h / 80 °C / Large scale View Scheme |
2-bromo-pyridine
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: isopropylmagnesium bromide / tetrahydrofuran / 1 h / 10 - 20 °C / Inert atmosphere 1.2: 4 h / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 20 h / Reflux 3.1: 5%-palladium/activated carbon / methanol / 4 h / 30 °C / 2068.65 Torr / Inert atmosphere; Autoclave View Scheme |
4-chlorobenzaldehyde
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: isopropylmagnesium bromide / tetrahydrofuran / 1 h / 10 - 20 °C / Inert atmosphere 1.2: 4 h / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 20 h / Reflux 3.1: 5%-palladium/activated carbon / methanol / 4 h / 30 °C / 2068.65 Torr / Inert atmosphere; Autoclave View Scheme |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Stage #1: 4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine With (+)-dibenzoyl-D-tartaric acid monohydrate In acetic acid methyl ester Stage #2: With D-tartaric acid In ethanol at 20℃; Stage #3: With sodium hydroxide In water | 99.6% |
With (R)-Mandelic Acid In methanol at 60℃; for 2h; Reflux; | 40% |
Stage #1: 4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine With (S)-2-acetylamino-3-phenylpropanoic acid In ethyl acetate Heating; Stage #2: With Cbz-Met-OH In acetonitrile Heating; | 38.2% |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
menthyl 4-chlorobutyrate
(R/S)-bepotastine L-menthyl ester
Conditions | Yield |
---|---|
Stage #1: menthyl 4-chlorobutyrate With sodium iodide for 5h; Heating / reflux; Stage #2: 4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine With potassium carbonate for 1h; Product distribution / selectivity; Heating / reflux; | 99% |
Stage #1: menthyl 4-chlorobutyrate With sodium iodide In 4-methyl-2-pentanone for 5h; Reflux; Stage #2: 4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine With potassium carbonate In 4-methyl-2-pentanone for 1h; Reflux; | 99% |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-bromobutanoate
(R/S)-bepotastine L-menthyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 7h; Product distribution / selectivity; Heating / reflux; | 99% |
With potassium carbonate In acetone for 7h; Reflux; | 99% |
With potassium carbonate In acetone for 7h; Reflux; | 99% |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
Stage #1: 4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine With (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate In acetic acid methyl ester Stage #2: With L-Tartaric acid In ethanol Stage #3: With sodium hydroxide In water | 98.6% |
With (S)-2-acetylamino-3-phenylpropanoic acid In ethyl acetate at 50 - 60℃; | 45.4% |
With (S)-Mandelic acid In methanol at 60℃; for 2h; Reflux; | 42% |
Multi-step reaction with 2 steps 1: ethyl acetate / 1 h / 65 °C / Large scale 2: hydrogenchloride / water / Large scale View Scheme |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
(S)-2-acetylamino-3-phenylpropanoic acid
Conditions | Yield |
---|---|
In ethyl acetate at 65℃; for 1h; Solvent; Temperature; Large scale; | 80% |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
3,4-Diacetoxy-benzoesaeure
Conditions | Yield |
---|---|
Stage #1: 3,4-Diacetoxy-benzoesaeure With phosphorus pentachloride In dichloromethane at 0 - 10℃; for 2h; Stage #2: 4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 78.1% |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine In N,N-dimethyl-formamide at 60 - 80℃; for 4h; | 54.9% |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
(S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide; acetone at 45℃; for 0.166667h; Solvent; Temperature; | 40% |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
3-methoxy-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine In N,N-dimethyl-formamide at 60 - 80℃; for 4h; | 31.6% |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
2-bromoethanol
2-[4-[(4-chlorophenyl)-pyridin-2-ylmethoxy]-1-piperidyl]ethanol
Conditions | Yield |
---|---|
With potassium carbonate In acetone | 0.64 g (56%) |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
2-(2-bromoethyl)isoindoline-1,3-dione
hydrazine hydrate
2-[4-[(4-chlorophenyl)-pyridin-2-ylmethoxy]-1-piperidyl]ethylamine
Conditions | Yield |
---|---|
With sodium hydroxide; potassium carbonate In 1,4-dioxane; ethanol | 3.50 g (41%) |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Ethyl 3-bromopropionate
ethyl 3-[4-[(4-chlorophenyl)-pyridin-2-ylmethoxy]-1-piperidyl]propionate
Conditions | Yield |
---|---|
With potassium carbonate In 1,4-dioxane; methanol; chloroform | 1.78 g (67%) |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
4-bromoethylbutanoate
Conditions | Yield |
---|---|
With potassium carbonate In methanol; chloroform; acetone | 6.26 g (91%) |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
A
5-chloro-2-pentanone
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
B
4-chloro-butyric acid propyl ester
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
B
4-bromo-trans-crotonic acid ethyl ester
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
B
4-chloro-1-phenylbutan-1-one
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
B
4'-tert-butyl-4-chlorobutyrophenone
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
B
N,N-dimethyl-4-chlorobutyramide
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
With potassium carbonate In 1,4-dioxane | 1.51 g (84%) |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
With potassium carbonate In 1,4-dioxane; methanol; chloroform | 1.83 g (54%) |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
With potassium carbonate In methanol; chloroform; acetone | 1.55 g (91%) |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
Conditions | Yield |
---|---|
With potassium carbonate In 1,4-dioxane | 0.52 g (20%) |
4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine
2-((3-bromopropyl)thio)benzo[d]thiazole
Conditions | Yield |
---|---|
With potassium carbonate In methanol; chloroform; acetone | 0.52 g (41%) |
Molecular Structure of 2-[(4-Chlorophenyl)(4-piperidinyloxy)methyl]pyridine (CAS NO.122368-54-1):
Systematic Name: 2-[(4-Chlorophenyl)(piperidin-4-yloxy)methyl]pyridine
Molecular Formula: C17H19ClN2O
Molecular Weight: 302.80
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 4
Nominal Mass: 302
Average Mass: 302.7986
Monoisotopic Mass: 302.118591
Index of Refraction: 1.601
Molar Refractivity: 85.178 cm3
Molar Volume: 248.708 cm3
Surface Tension: 51.295 dyne/cm
Density: 1.217 g/cm3
Flash Point: 208.825 °C
Enthalpy of Vaporization: 67.573 kJ/mol
Boiling Point: 421.68 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25 °C
SMILES: Clc1ccc(cc1)C(OC2CCNCC2)c3ncccc3
InChI: InChI=1/C17H19ClN2O/c18-14-6-4-13(5-7-14)17(16-3-1-2-10-20-16)21-15-8-11-19-12-9-15/h1-7,10,15,17,19H,8-9,11-12H2
InChIKey: OTZYADIPHOGUDN-UHFFFAOYAW
2-[(4-Chlorophenyl)(4-piperidinyloxy)methyl]pyridine (CAS NO.122368-54-1), its Synonyms are Pyridine,2-[(4-chlorophenyl)(4-piperidinyloxy)methyl]- ; (RS)-4-[(4-Chlorophenyl)(2-pyridyl)methoxy]piperidine .
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