• Name

  Paliperidone Palmitate [USAN]

• EINECS
• CAS No. 199739-10-1
• Article Data4
• CAS DataBase
• Density 1.196 g/cm³
• Solubility
• Melting Point
• Formula C₃₉H₅₇FN₄O₄
• Boiling Point 736.308 °C at 760 mmHg
• Molecular Weight 664.904
• Flash Point 399.105 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Hexadecanoic acid, 3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl)ethyl)-6,7,8,9-tetrahydro-2-methyl-4-oxo-4H-pyrido(1,2-a)pyrimidin-9-yl ester;Ro 92670;RO92670;Paliperidone Palmitate;(9RS)-3-(2-(4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-2-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidin-9-yl hexadecanoate;
• PSA 90.46000
• LogP 9.05140

Synthetic route

623-65-4

palmitic anhydride

144598-75-4

paliperidone

199739-10-1

paliperidone palmitate

Conditions

Conditions	Yield
Stage #1: palmitic anhydride; paliperidone With dmap In toluene at 20 - 70℃; for 3h; Stage #2: With tert-butyl methyl ether In toluene at 10℃; for 1h; Product distribution / selectivity;	88.5%

57-10-3

1-hexadecylcarboxylic acid

144598-75-4

paliperidone

199739-10-1

paliperidone palmitate

Conditions

Conditions	Yield
With dmap; pivaloyl chloride; triethylamine In tetrahydrofuran at 20℃; for 24h; Product distribution / selectivity;	80%

1415488-05-9

3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-one palmitate ester

84163-13-3

6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride

199739-10-1

paliperidone palmitate

Conditions

Conditions	Yield
Stage #1: 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride With potassium carbonate In acetonitrile at 25 - 60℃; for 1.16667h; Stage #2: 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-one palmitate ester With tetrabutylammomium bromide; potassium iodide at 20 - 75℃; for 14h;	80%
Stage #1: 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride With potassium carbonate In acetonitrile at 25 - 60℃; for 1.16667h; Stage #2: 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-one palmitate ester With tetra-(n-butyl)ammonium iodide; potassium iodide In acetonitrile at 25 - 75℃; for 16h;	80%

144598-75-4

paliperidone

112-67-4

n-hexadecanoyl chloride

199739-10-1

paliperidone palmitate

Conditions

Conditions	Yield
Stage #1: paliperidone With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: n-hexadecanoyl chloride In N,N-dimethyl-formamide at 0℃; for 5h; Product distribution / selectivity;	53.1%
With dmap; triethylamine In dichloromethane at 15℃; for 8h; Temperature;

1172995-09-3

3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one sodium

112-67-4

n-hexadecanoyl chloride

199739-10-1

paliperidone palmitate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 2h;	10 %Chromat.

57-10-3

1-hexadecylcarboxylic acid

199739-10-1

paliperidone palmitate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dmap; triethylamine / dichloromethane / 0.25 h / 25 - 30 °C 1.2: 2 h / 25 - 40 °C 2.1: potassium carbonate / acetonitrile / 1.17 h / 25 - 60 °C 2.2: 14 h / 20 - 75 °C View Scheme

199739-10-1

paliperidone palmitate

144598-75-4

paliperidone

Conditions

Conditions	Yield
Stage #1: paliperidone palmitate With hydrogenchloride In water at 75 - 80℃; for 2h; Stage #2: With sodium hydroxide In methanol; dichloromethane; water; isopropyl alcohol at 10 - 30℃; for 1h; pH=10 - 12; Reflux;	90%
With hydrogenchloride In water at 75 - 80℃; for 2h;	90%

199739-10-1

paliperidone palmitate

A

913728-82-2

3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7-dihydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

B

913728-83-3

3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-9-pentadecyl-4H-pyrido[1,2-a]pyrimidin-4-one

C

144598-75-4

paliperidone

Conditions

Conditions	Yield
Product distribution / selectivity; X-irradiation;

...Expand

Paliperidone Palmitate Specification