• Name

  Amisulpride

• EINECS 275-831-7
• CAS No. 71675-85-9
• Article Data9
• CAS DataBase
• Density 1.2 g/cm³
• Solubility DMSO: ≥5 mg/mL
• Melting Point 124-128 °C
• Formula C₁₇H₂₇N₃O₄S
• Boiling Point 558.9 °C at 760 mmHg
• Molecular Weight 369.485
• Flash Point 291.8 °C
• Transport Information
• Appearance Off-white solid
• Safety 22-24/25
• Risk Codes 22
• Molecular Structure
• Hazard Symbols Xn
• Synonyms 4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-o-anisamide;Aminosultopride;4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxy-benzamide;Amisulprida [INN-Spanish];Benzamide, 4-amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxy-;Benzamide,4-amino-N-[(1-ethyl-2- pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2- methoxy-;4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-anisamid;4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide;Amisulpridum [INN-Latin];Solian;DAN 2163;Methyl ammonia mosapride;
• PSA 110.11000
• LogP 3.27590

Synthetic route

26116-12-1

1-ethyl-2-pyrrolidinemethanamine

541-41-3

chloroformic acid ethyl ester

71675-85-9

amisulpride

Conditions

Conditions	Yield
In triethylamine; acetone	100%
In triethylamine; acetone	84%

26116-12-1

1-ethyl-2-pyrrolidinemethanamine

methyl 4-amino-5-(ethylsulfonyl)-2-methoxybenzoate

71675-85-9

amisulpride

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 83℃; for 20h; Reagent/catalyst; Solvent; Temperature;	96.5%

26116-12-1

1-ethyl-2-pyrrolidinemethanamine

2-methoxy-4-amino-5-ethanesulfonylbenzoyl chloride

71675-85-9

amisulpride

Conditions

Conditions	Yield
In dichloromethane at 20 - 40℃; for 6h; Temperature;	89.4%

26116-12-1

1-ethyl-2-pyrrolidinemethanamine

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

71675-85-9

amisulpride

Conditions

Conditions	Yield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 10 - 20℃; for 1.5h; Stage #2: 1-ethyl-2-pyrrolidinemethanamine With triethylamine In acetonitrile at 80℃; for 2h;	86.8%
With C36H24B4N2O3 In toluene for 14h; Molecular sieve; Reflux; chemoselective reaction;	76%
With chloroformic acid ethyl ester; triethylamine In acetone at 0 - 30℃;	70%

26116-12-1

1-ethyl-2-pyrrolidinemethanamine

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

541-41-3

chloroformic acid ethyl ester

71675-85-9

amisulpride

Conditions

Conditions	Yield
With triethylamine In water; acetone	61%

...Expand

74-96-4

ethyl bromide

176849-91-5

4-amino-N-(1-ethyl-pyrrolidin-2-ylmethyl)-5-iodo-2-methoxy-benzamide

71675-85-9

amisulpride

Conditions

Conditions

Yield

Stage #1: ethyl bromide; 4-amino-N-(1-ethyl-pyrrolidin-2-ylmethyl)-5-iodo-2-methoxy-benzamide With 1,1'-bis-(diphenylphosphino)ferrocene; sodium metabisulfite; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tin; potassium hydrogenphosphate trihydrate; tetrabutylammomium bromide In dimethyl sulfoxide at 100℃; for 10h; Inert atmosphere; Schlenk technique; Stage #2: With potassium carbonate In methanol at 20℃; for 2h;

61%

74-96-4

ethyl bromide

C19H29N3O5S

71675-85-9

amisulpride

Conditions

Conditions	Yield
Stage #1: ethyl bromide; C19H29N3O5S With 1,1'-bis-(diphenylphosphino)ferrocene; sodium metabisulfite; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tin; potassium hydrogenphosphate trihydrate; tetrabutylammomium bromide In dimethyl sulfoxide at 100℃; for 10h; Inert atmosphere; Stage #2: With potassium carbonate In methanol at 20℃; for 2h;	61%

71675-87-1

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

1-ethyl-2-aminomethylpyrrolidine hydrochloride

71675-85-9

amisulpride

Conditions

Conditions	Yield
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1-ethyl-2-aminomethylpyrrolidine hydrochloride With triethylamine In dichloromethane at 20℃;	29.7%

27492-84-8

Methyl 4-amino-2-methoxybenzoate

71675-85-9

amisulpride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: bromine / methanol / 5 - 15 °C / Industry scale 2.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 3.1: sodium hydroxide; water / methanol / 65 °C / Industry scale 3.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale 4.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C 5.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme
Multi-step reaction with 4 steps 1.1: bromine / methanol / 5 - 15 °C / Industry scale 2.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 3.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale 3.2: 60 - 65 °C / Industry scale 3.3: pH 4 - 4.5 / Industry scale 4.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme

65-49-6

4-Aminosalicylic acid

71675-85-9

amisulpride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale 2.1: bromine / methanol / 5 - 15 °C / Industry scale 3.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 4.1: sodium hydroxide; water / methanol / 65 °C / Industry scale 4.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale 5.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C 6.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme
Multi-step reaction with 5 steps 1.1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale 2.1: bromine / methanol / 5 - 15 °C / Industry scale 3.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 4.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale 4.2: 60 - 65 °C / Industry scale 4.3: pH 4 - 4.5 / Industry scale 5.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme

59168-56-8

methyl 4-amino-2-methoxy-5-thiocyanatobenzoate

71675-85-9

amisulpride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 2.1: sodium hydroxide; water / methanol / 65 °C / Industry scale 2.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale 3.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C 4.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 2.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale 2.2: 60 - 65 °C / Industry scale 2.3: pH 4 - 4.5 / Industry scale 3.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme

2-methoxy-4-amino-5-ethylthio benzoic acid

71675-85-9

amisulpride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C 2: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme

1119455-01-4

methyl 4-amino-5-(ethylthio)-2-methoxybenzoate

71675-85-9

amisulpride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / methanol / 65 °C / Industry scale 1.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale 2.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C 3.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme

64-18-6

formic acid

71675-85-9

amisulpride

4-formylamino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
With acetic anhydride at 5 - 20℃;	83%

32634-66-5

Di-p-toluoyl-L-tartaric acid

71675-85-9

amisulpride

(S)-4-amino-N-((1-ethylpyrrolidin-2-yl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide (2R,3R)-bis((4-methylbenzoyl)oxy)succinic acid salt

Conditions

Conditions	Yield
In water; acetonitrile at 70℃; for 0.25h;	79.4%

71675-85-9

amisulpride

(-)-Amisulpride

Conditions

Conditions	Yield
With D-Malic acid In ethanol at 20℃; for 2h;	64.7%

71675-85-9

amisulpride

17465-86-0

cyclomaltooctaose

C48H80O40*C17H27N3O4S

Conditions

Conditions	Yield
In methanol; water for 24h;

64-19-7

acetic acid

71675-85-9

amisulpride

4-ethylamino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃;	309 mg

67-64-1

acetone

71675-85-9

amisulpride

4-isopropylamino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In N,N-dimethyl-formamide; acetone at 40℃; Cooling with ice;	550 mg

123-38-6

propionaldehyde

71675-85-9

amisulpride

4-n-propylamino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane	518 mg

100-52-7

benzaldehyde

71675-85-9

amisulpride

4-benzylamino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; trifluoroacetic acid In N,N-dimethyl-formamide at 40℃;	366 mg

71675-85-9

amisulpride

4-dimethylamino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic anhydride / 5 - 20 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 5 - 60 °C 3: 21 h / 30 °C View Scheme

71675-85-9

amisulpride

4-ethylmethylamino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic anhydride / 5 - 20 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 5 - 60 °C 3: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 17 h / 20 °C View Scheme

71675-85-9

amisulpride

4-methylamino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride / 5 - 20 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 5 - 60 °C View Scheme

548-26-5, 602-47-1, 17372-87-1

Eosin Y

71675-85-9

amisulpride

C17H27N3O4S*C20H8Br4O5

Conditions

Conditions	Yield
pH=3.3;

32634-68-7

(2S,3S)-di-4-toluoyltartaric acid

71675-85-9

amisulpride

(R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide di-p-toluoyl tartrate

Conditions

Conditions	Yield
In acetonitrile at 75℃; for 0.5h; Temperature; Inert atmosphere; Large scale;	26.73 kg

71675-85-9

amisulpride

A

(-)-Amisulpride

B

(R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
With diethylamine In acetonitrile at 30℃; under 26252.6 Torr; Resolution of racemate; Large scale;	A 3752.2 g B 2346 g

71675-85-9

amisulpride

(R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile / 0.5 h / 75 °C / Inert atmosphere; Large scale 2: hydrogenchloride / water; tert-butyl methyl ether / 0.25 h / Inert atmosphere; Large scale View Scheme

71675-85-9

amisulpride

(S)-(-)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide D-tartrate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethylamine / acetonitrile / 30 °C / 26252.6 Torr / Resolution of racemate; Large scale 2: methanol / 0.75 h / 22 °C View Scheme

Amisulpride Chemical Properties

Amisulpride Uses

Amisulpride Toxicity Data With Reference

Amisulpride Safety Profile