Product Name

Synthetic route

(-)-Methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3β-carboxylate
214335-16-7

(-)-Methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3β-carboxylate

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

Conditions
ConditionsYield
With sodium methylate In methanol epimerization; Heating;100%
With sodium methylate In methanol for 24h; Heating;86%
With sodium methylate In methanol at 60℃; for 6h;
arecoline
63-75-2

arecoline

(4-chlorphenyl)magnesium bromide
873-77-8

(4-chlorphenyl)magnesium bromide

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

Conditions
ConditionsYield
Stage #1: arecoline; (4-chlorphenyl)magnesium bromide In diethyl ether at -10℃; Addition;
Stage #2: With O,O'-dibenzoyl-L-tartaric acid Racemate resolution; Further stages.;
arecoline
63-75-2

arecoline

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 56 percent / diethyl ether / 0.5 h / -10 °C
3: 86 percent / NaOMe / methanol / 24 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: tert-butyl methyl ether; diethyl ether / 3 h / -20 - -5 °C / Inert atmosphere
2: O,O'-dibenzoyl-L-tartaric acid / methanol / 0.5 h / 60 - 65 °C
3: sodium methylate / methanol / 6 h / 60 °C
View Scheme
(4-chlorphenyl)magnesium bromide
873-77-8

(4-chlorphenyl)magnesium bromide

(+-)-2-hydroxy-1-phenyl-propan-1-one

(+-)-2-hydroxy-1-phenyl-propan-1-one

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 56 percent / diethyl ether / 0.5 h / -10 °C
3: 86 percent / NaOMe / methanol / 24 h / Heating
View Scheme
(±)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3β-carboxylate

(±)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3β-carboxylate

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 86 percent / NaOMe / methanol / 24 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: O,O'-dibenzoyl-L-tartaric acid / methanol / 0.5 h / 60 - 65 °C
2: sodium methylate / methanol / 6 h / 60 °C
View Scheme
methyl 4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate

methyl 4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium diisopropyl amide / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere
2: O,O'-dibenzoyl-L-tartaric acid / methanol / 0.5 h / 60 - 65 °C
3: sodium methylate / methanol / 6 h / 60 °C
View Scheme
(4-chlorphenyl)magnesium bromide
873-77-8

(4-chlorphenyl)magnesium bromide

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tert-butyl methyl ether; diethyl ether / 3 h / -20 - -5 °C / Inert atmosphere
2: O,O'-dibenzoyl-L-tartaric acid / methanol / 0.5 h / 60 - 65 °C
3: sodium methylate / methanol / 6 h / 60 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-4β-(4-Chlorophenyl)-3α-(hydroxymethyl)-1-methylpiperidine
263769-24-0

(+)-4β-(4-Chlorophenyl)-3α-(hydroxymethyl)-1-methylpiperidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;92%
With lithium aluminium tetrahydride In tetrahydrofuran92%
Stage #1: (+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;
Stage #2: With water; ammonium chloride In tetrahydrofuran		92%
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Ambient temperature;84%
With lithium aluminium tetrahydride In tetrahydrofuran
acetamide oxime
118493-85-9, 117771-39-8, 1141922-26-0

acetamide oxime

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(3R,4S)-4-(4-Chloro-phenyl)-1-methyl-3-(3-methyl-[1,2,4]oxadiazol-5-yl)-piperidine

(3R,4S)-4-(4-Chloro-phenyl)-1-methyl-3-(3-methyl-[1,2,4]oxadiazol-5-yl)-piperidine

Conditions
ConditionsYield
With molecular sieve; sodium hydride In tetrahydrofuran Heating;74%
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(3R,4S)-4-(4-chlorophenyl)piperidine-3-carboxylic acid methyl ester

(3R,4S)-4-(4-chlorophenyl)piperidine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
Stage #1: (+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate With carbonochloridic acid 1-chloro-ethyl ester; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In dichloromethane for 1.5h; Heating;
Stage #2: In methanol for 1h; Heating; Further stages.;		67%
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-4β-(4-Chlorophenyl)-1-methylpiperidine-3α-carboxylic Acid
263769-44-4

(+)-4β-(4-Chlorophenyl)-1-methylpiperidine-3α-carboxylic Acid

Conditions
ConditionsYield
With hydrogenchloride Hydrolysis; Heating;
With hydrogenchloride Heating;
With hydrogenchloride Hydrolysis; Heating;
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

2-[(3R,4S)-4-(4-Chloro-phenyl)-piperidin-3-ylmethylsulfanyl]-ethanol
896710-05-7

2-[(3R,4S)-4-(4-Chloro-phenyl)-piperidin-3-ylmethylsulfanyl]-ethanol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / LiAlH4 / tetrahydrofuran
2: 86 percent / Ph3P; I2; imidazole
3: 88 percent / Cs2CO3
4: 80 percent / 1-chloroethyl chloroformate; proton sponge / CH2Cl2
5: 56 percent / LiAlH4 / tetrahydrofuran
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

2-[(3R,4S)-4-(4-Chloro-phenyl)-piperidin-3-ylmethylsulfanyl]-1-piperidin-1-yl-ethanone
896710-06-8

2-[(3R,4S)-4-(4-Chloro-phenyl)-piperidin-3-ylmethylsulfanyl]-1-piperidin-1-yl-ethanone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / LiAlH4 / tetrahydrofuran
2: 86 percent / Ph3P; I2; imidazole
3: 88 percent / Cs2CO3
4: 80 percent / 1-chloroethyl chloroformate; proton sponge / CH2Cl2
5: methanol
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-(3R,4S)-4-(4-chlorophenyl)-3-(iodomethyl)-1-methylpiperidine
807342-01-4

(+)-(3R,4S)-4-(4-chlorophenyl)-3-(iodomethyl)-1-methylpiperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / LiAlH4 / tetrahydrofuran
2: 86 percent / Ph3P; I2; imidazole
View Scheme
Multi-step reaction with 2 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]acetic acid methyl ester
807342-02-5

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]acetic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / LiAlH4 / tetrahydrofuran
2: 86 percent / Ph3P; I2; imidazole
3: 88 percent / Cs2CO3
View Scheme
Multi-step reaction with 3 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-trans-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]ethanol
807342-04-7

(+)-trans-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]ethanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran
2: 86 percent / Ph3P; I2; imidazole
3: 88 percent / Cs2CO3
4: 56 percent / LiAlH4 / tetrahydrofuran
View Scheme
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 82 percent / LiAlH4 / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methylsulfanyl]acetic acid methyl ester
807342-26-3

(+)-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methylsulfanyl]acetic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran
2: 86 percent / Ph3P; I2; imidazole
3: 88 percent / Cs2CO3
4: 80 percent / 1-chloroethyl chloroformate; proton sponge / CH2Cl2
View Scheme
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 80 percent / 1,8-bis(dimethylamino)naphthalene; α-chloroethyl chloroformate / CH2Cl2 / 2.5 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: carbonochloridic acid 1-chloro-ethyl ester; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 2.5 h / Heating / reflux
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-trans-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]-1-(piperidin-1-yl)ethanone
807342-17-2

(+)-trans-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]-1-(piperidin-1-yl)ethanone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran
2: 86 percent / Ph3P; I2; imidazole
3: 88 percent / Cs2CO3
4: methanol
View Scheme
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 92 percent / methanol / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: methanol / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-(3R,4S)-4-(4-chlorophenyl)-3-[(2-methoxyethylsulfanyl)methyl]-1-methylpiperidine
807342-06-9

(+)-(3R,4S)-4-(4-chlorophenyl)-3-[(2-methoxyethylsulfanyl)methyl]-1-methylpiperidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2.1: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3.1: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4.1: 82 percent / LiAlH4 / tetrahydrofuran / 20 °C
5.1: NaH / tetrahydrofuran / 0.17 h / 0 °C
5.2: 65 percent / tetra-n-butylammonium iodide / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3.1: caesium carbonate / acetonitrile / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
5.1: sodium hydride / tetrahydrofuran / 0 °C
5.2: 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]ethanol

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]ethanol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 82 percent / LiAlH4 / tetrahydrofuran / 20 °C
5: 69 percent / aq. H2O2; CH3COOH / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
5: dihydrogen peroxide / water; acetic acid / 2.5 h / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]-N-methylacetamide
807342-14-9

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]-N-methylacetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 72 percent / methanol / 24 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: methanol / 24 h / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-(3R,4S)-4-(4-chlorophenyl)-3-[(2-methoxyethylsulfinyl)methyl]-1-methylpiperidine

(+)-(3R,4S)-4-(4-chlorophenyl)-3-[(2-methoxyethylsulfinyl)methyl]-1-methylpiperidine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2.1: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3.1: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4.1: 82 percent / LiAlH4 / tetrahydrofuran / 20 °C
5.1: NaH / tetrahydrofuran / 0.17 h / 0 °C
5.2: 65 percent / tetra-n-butylammonium iodide / tetrahydrofuran / 20 °C
6.1: 61 percent / aq. H2O2; CH3COOH / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3.1: caesium carbonate / acetonitrile / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
5.1: sodium hydride / tetrahydrofuran / 0 °C
5.2: 20 °C
6.1: dihydrogen peroxide / water; acetic acid / 2.5 h / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methylsulfanyl]acetamide
807342-27-4

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methylsulfanyl]acetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 90 percent / NH3(gas) / 2-methyl-propan-2-ol / 72 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: carbonochloridic acid 1-chloro-ethyl ester; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 2.5 h / Heating / reflux
5: ammonia / tert-butyl alcohol / 72 h / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]acetamide
807342-12-7

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]acetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 95 percent / NH3 (gas) / 2-methyl-propan-2-ol / 72 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: ammonia / tert-butyl alcohol / 72 h / 20 °C / Sealed tube
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]-N,N-dimethylacetamide
807342-15-0

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]-N,N-dimethylacetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 91 percent / methanol / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: methanol / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]acetic acid methyl ester

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]acetic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 80 percent / aq. H2O2; CH3COOH / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: dihydrogen peroxide / water; acetic acid / 2.5 h / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]-N-hydroxyacetamide
807342-13-8

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]-N-hydroxyacetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 76 percent / hydroxylamine hydrochloride; KOH / methanol / 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: potassium hydroxide; hydroxylamine hydrochloride / methanol / 2 h / 5 - 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methanesulfinyl]acetamide

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methanesulfinyl]acetamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 90 percent / NH3(gas) / 2-methyl-propan-2-ol / 72 h / 20 °C
5: 73 percent / aq. H2O2; CH3COOH / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: carbonochloridic acid 1-chloro-ethyl ester; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 2.5 h / Heating / reflux
5: ammonia / tert-butyl alcohol / 72 h / 20 °C
6: dihydrogen peroxide / water; acetic acid / 2.5 h / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-acetic acid 2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]ethyl ester
807342-08-1

(+)-acetic acid 2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 82 percent / LiAlH4 / tetrahydrofuran / 20 °C
5: 70 percent / 4-(dimethylamino)pyridine; pyridine / 2 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
5: pyridine / dmap / 2 h / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]acetamide
807342-18-3

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]acetamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 95 percent / NH3 (gas) / 2-methyl-propan-2-ol / 72 h / 20 °C
5: 69 percent / aq. H2O2; CH3COOH / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: ammonia / tert-butyl alcohol / 72 h / 20 °C / Sealed tube
5: dihydrogen peroxide / water; acetic acid / 2.5 h / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]-N-methylacetamide

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]-N-methylacetamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 72 percent / methanol / 24 h / 20 °C
5: 80 percent / aq. H2O2; CH3COOH / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: methanol / 24 h / 20 °C
5: dihydrogen peroxide / water; acetic acid / 2.5 h / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-(3R,4S)-[[4-(4-chlorophenyl)-1-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)methylsulfanyl]methyl]piperidine
807342-24-1

(+)-(3R,4S)-[[4-(4-chlorophenyl)-1-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)methylsulfanyl]methyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2.1: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3.1: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4.1: NaH / tetrahydrofuran / 2.5 h / Heating
4.2: 79 percent / 4A molecular sieves / tetrahydrofuran / 16 h / Heating
View Scheme
Multi-step reaction with 4 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3.1: caesium carbonate / acetonitrile / 20 °C
4.1: sodium hydride / tetrahydrofuran / 2.5 h / Heating / reflux
4.2: 16 h / Heating / reflux; Molecular sieve
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-acetic acid 2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]ethyl ester

(+)-acetic acid 2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 82 percent / LiAlH4 / tetrahydrofuran / 20 °C
5: 70 percent / 4-(dimethylamino)pyridine; pyridine / 2 h / 20 °C
6: 82 percent / aq. H2O2; CH3COOH / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
5: pyridine / dmap / 2 h / 20 °C
6: dihydrogen peroxide / water; acetic acid / 2.5 h / 20 °C
View Scheme
(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate
263769-22-8

(+)-methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]-N,N-dimethylacetamide

(+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methanesulfinyl]-N,N-dimethylacetamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 86 percent / PPh3; I2; imidazole / CH2Cl2 / 2.5 h / Heating
3: 88 percent / Cs2CO3 / acetonitrile / 20 °C
4: 91 percent / methanol / 20 °C
5: 87 percent / aq. H2O2; CH3COOH / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / Heating / reflux
3: caesium carbonate / acetonitrile / 20 °C
4: methanol / 20 °C
5: dihydrogen peroxide / water; acetic acid / 2.5 h / 20 °C
View Scheme

(3R,4S)-4-(4-Chlorophenyl)-1-methylpiperidine-3-carboxylic acid methyl ester Specification

The systematic name of (3R,4S)-4-(4-Chlorophenyl)-1-methylpiperidine-3-carboxylic acid methyl ester is methyl (3R,4S)-4-(4-chlorophenyl)-1-methylpiperidine-3-carboxylate. With the CAS registry number 263769-22-8, it is also named as 3-Piperidinecarboxylicacid, 4-(4-chlorophenyl)-1-methyl-, methyl ester, (3R,4S)-. The product's molecular formula is C14H18ClNO2 and its molecular weight is 267.75. 

The other characteristics of (3R,4S)-4-(4-Chlorophenyl)-1-methylpiperidine-3-carboxylic acid methyl ester can be summarized as: (1)ACD/LogP: 2.55; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.03; (4)ACD/LogD (pH 7.4): 1.66; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 6.61; (7)ACD/KOC (pH 5.5): 1.54; (8)ACD/KOC (pH 7.4): 75.26; (9)H bond acceptors: 3; (10)H bond donors: 0; (11)Freely Rotating Bonds: 3; (12)Polar Surface Area: 29.54 Å2; (13)Index of Refraction: 1.531; (14)Molar Refractivity: 71.62 cm3; (15)Molar Volume: 231.2 cm3; (16)Polarizability: 28.39×10-24cm3; (17)Surface Tension: 39.4 dyne/cm; (18)Density: 1.157 g/cm3; (19)Flash Point: 161.5 °C; (20)Enthalpy of Vaporization: 58.74 kJ/mol; (21)Boiling Point: 343.5 °C at 760 mmHg; (22)Vapour Pressure: 7.01E-05 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
SMILES:Clc1ccc(cc1)[C@@H]2[C@@H](C(=O)OC)CN(C)CC2
InChI:InChI=1/C14H18ClNO2/c1-16-8-7-12(13(9-16)14(17)18-2)10-3-5-11(15)6-4-10/h3-6,12-13H,7-9H2,1-2H3/t12-,13+/m1/s1
InChIKey:GDFVYUDIAQQDTA-OLZOCXBDBP
Std. InChI:InChI=1S/C14H18ClNO2/c1-16-8-7-12(13(9-16)14(17)18-2)10-3-5-11(15)6-4-10/h3-6,12-13H,7-9H2,1-2H3/t12-,13+/m1/s1
Std. InChIKey:GDFVYUDIAQQDTA-OLZOCXBDSA-N

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