Product Name

  • Name

    Sertraline HCL

  • EINECS 200-659-6
  • CAS No. 79559-97-0
  • Article Data33
  • CAS DataBase
  • Density 1.37
  • Solubility DMSO: ~26 mg/mL
  • Melting Point 246-249 °C
  • Formula C17H17Cl2N.HCl
  • Boiling Point 416.3 °C at 760 mmHg
  • Molecular Weight 342.696
  • Flash Point 205.6 °C
  • Transport Information
  • Appearance White or white-like crystalline powder
  • Safety 22-24/25-36-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 79559-97-0 (Sertraline HCL)
  • Hazard Symbols IrritantXi
  • Synonyms 1-Naphthalenamine,4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-, hydrochloride, (1S,4S)-(9CI);(1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenaminehydrochloride;(1S,4S)-N-Methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenaminehydrochloride;Altruline;Aremis;Atruline;Cp 51974-1;Dominum;Gladem;Lesefer;Lustral;Selectra;Sosser;Stimuloton;Zolof;Zoloft;
  • PSA 12.03000
  • LogP 6.37250

Synthetic route

sertraline 4-methoxybenzoate

sertraline 4-methoxybenzoate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; nitromethane at 25 - 30℃; for 1h; Product distribution / selectivity;97%
Sertraline
79617-96-2

Sertraline

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In propan-1-ol at 30℃; for 1h; Product distribution / selectivity;96%
With hydrogenchloride In acetonitrile for 1h; Product distribution / selectivity;95%
With hydrogenchloride In octanol for 1h; Product distribution / selectivity;95%
(1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphtalenamine citrate
836597-67-2

(1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphtalenamine citrate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In acetonitrile at 20℃; for 1h; Product distribution / selectivity;95%
With hydrogenchloride In propan-1-ol; water at 20 - 70℃; for 1h; pH=0; Product distribution / selectivity;90%
(1S-cis)-4-(3,4 dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine mandelate

(1S-cis)-4-(3,4 dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine mandelate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methoxypropyl acetate at 20 - 70℃; for 3h; Product distribution / selectivity;95%
With N,N-dimethylacetamide hydrochloride In 4-methyl-2-pentanone at 20 - 80℃; for 1.5h; Product distribution / selectivity;94%
With N,N-dimethylacetamide hydrochloride In acetonitrile at 20℃; for 1h; Product distribution / selectivity;90%
sertraline adipate
928057-23-2

sertraline adipate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; nitromethane at 25 - 30℃; for 1h; Product distribution / selectivity;86%
(cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate
244223-89-0, 79617-97-3

(cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water Industrial scale;85%
With hydrogenchloride In acetonitrile at 0 - 15℃; for 0.5 - 1h; Product distribution / selectivity;82.6%
With hydrogenchloride In tert-Amyl alcohol at 25 - 30℃; for 8h; pH=2.0; Product distribution / selectivity;
C17H17Cl2N*C5H9NO4

C17H17Cl2N*C5H9NO4

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Stage #1: C17H17Cl2N*C5H9NO4 With sodium hydroxide In water; toluene at 80℃; for 3h;
Stage #2: With hydrogenchloride In ethanol pH=1.0; Heating;		83.68%
sertraline phthalate
928057-20-9

sertraline phthalate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; 4-methyl-2-pentanone at 25 - 70℃; for 3h; Product distribution / selectivity;79%
sertraline 4-methylbenzoate
928057-24-3

sertraline 4-methylbenzoate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; nitromethane at 25 - 30℃; for 1h; Product distribution / selectivity;79%
sertraline salicylate
928057-22-1

sertraline salicylate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; nitromethane at 25 - 30℃; for 1h; Product distribution / selectivity;73%
(+/-)-N-methyl-[(cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amine hydrochloride

(+/-)-N-methyl-[(cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amine hydrochloride

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Purification / work up;46%
hydrogenchloride
7647-01-0

hydrogenchloride

(1S,4S)-sertraline*(S)-mandelic acid
1357380-69-8

(1S,4S)-sertraline*(S)-mandelic acid

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
In water; isopropyl alcohol at 20℃; pH=1 - 2; Heating / reflux;
1S-cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine-mandelate
254731-40-3

1S-cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine-mandelate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Stage #1: 1S-cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine-mandelate With sodium hydroxide In water; ethyl acetate pH=2;
Stage #2: With hydrogenchloride In isopropyl alcohol pH=2;
sertraline acetate

sertraline acetate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol; toluene at 20 - 60℃; pH=1 - 2; Conversion of starting material;
With hydrogenchloride In water at 20 - 25℃; for 1h; pH=1 - 2;
With hydrogenchloride In isopropyl alcohol; toluene at 0 - 60℃; for 0.25 - 0.333333h; pH=1 - 2; Conversion of starting material;
With hydrogenchloride In isopropyl alcohol at 15 - 50℃; for 0.5h; pH=1 - 2; Conversion of starting material;
acetic acid
64-19-7

acetic acid

Sertraline
79617-96-2

Sertraline

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Stage #1: acetic acid; Sertraline In water at 5 - 25℃; for 1.33333h;
Stage #2: With hydrogenchloride In water at 5 - 15℃; for 1.25h;
(1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine

(1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine

A

trans-(1S,4R)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride
79896-31-4

trans-(1S,4R)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrochloride

B

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; water Product distribution / selectivity;
With hydrogenchloride In water; ethyl acetate Product distribution / selectivity;
With hydrogenchloride In water; isopropyl alcohol Product distribution / selectivity;
N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine
79560-20-6

N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine

4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine hydrochloride

4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine hydrochloride

B

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Stage #1: N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine With hydrogen; pyridine hydrochloride; 50% Pd/C In methanol at 25 - 35℃; for 6h;
Stage #2: With hydrogenchloride In methanol; water pH=1 - 2; Product distribution / selectivity;
Stage #1: N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine With hydrogen; pyridine hydrochloride; platinum on carbon In methanol at 25 - 35℃; for 0.5h;
Stage #2: With hydrogenchloride In methanol; water pH=1 - 2; Product distribution / selectivity;
Stage #1: N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine With hydrogen; N,N-dimethylacetamide hydrochloride; 50% Pd/C In methanol at 25 - 35℃; for 4h;
Stage #2: With hydrogenchloride In methanol; water pH=1 - 2; Product distribution / selectivity;
(S)-N-(4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-ylidene)methanamine
312620-93-2

(S)-N-(4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-1(2H)-ylidene)methanamine

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere
2: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere; Autoclave
2: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
α-naphthol
90-15-3

α-naphthol

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: aluminum (III) chloride / 4 h / 100 °C / Inert atmosphere
2: chiral HPLC / Resolution of racemate
3: methanol; dichloromethane / 96 h / 20 °C / Inert atmosphere; Molecular sieve
4: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere
5: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: aluminum (III) chloride / 4 h / 100 °C / Inert atmosphere
2: chiral HPLC / Resolution of racemate
3: methanol; dichloromethane / 96 h / 20 °C / Inert atmosphere; Molecular sieve
4: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere; Autoclave
5: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: aluminum (III) chloride / 1.5 h / 100 °C / Inert atmosphere
2.1: borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 6 h / 25 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: sodium carbonate / hexane / 0.33 h / -40 °C / Inert atmosphere
4.2: 40 h / -40 °C / Inert atmosphere
5.1: water; sodium sulfite / hexane; ethyl acetate / 12 h / 20 °C / Inert atmosphere
6.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
6.2: 0 - 20 °C / Inert atmosphere
7.1: hydrogen / methanol; dichloromethane; water / 5 h / 20 °C / Inert atmosphere
8.1: hydrogenchloride / diethyl ether / 20 °C / Inert atmosphere
View Scheme
4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one
79560-19-3

4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: chiral HPLC / Resolution of racemate
2: methanol; dichloromethane / 96 h / 20 °C / Inert atmosphere; Molecular sieve
3: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere
4: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: chiral HPLC / Resolution of racemate
2: methanol; dichloromethane / 96 h / 20 °C / Inert atmosphere; Molecular sieve
3: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere; Autoclave
4: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 6 h / 25 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
2.2: 0 - 20 °C / Inert atmosphere
3.1: sodium carbonate / hexane / 0.33 h / -40 °C / Inert atmosphere
3.2: 40 h / -40 °C / Inert atmosphere
4.1: water; sodium sulfite / hexane; ethyl acetate / 12 h / 20 °C / Inert atmosphere
5.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
5.2: 0 - 20 °C / Inert atmosphere
6.1: hydrogen / methanol; dichloromethane; water / 5 h / 20 °C / Inert atmosphere
7.1: hydrogenchloride / diethyl ether / 20 °C / Inert atmosphere
View Scheme
(4S)-4-(3,4-dichlorophenyl)-1-tetralone
79560-19-3, 79836-44-5, 124379-29-9

(4S)-4-(3,4-dichlorophenyl)-1-tetralone

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanol; dichloromethane / 96 h / 20 °C / Inert atmosphere; Molecular sieve
2: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere
3: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: methanol; dichloromethane / 96 h / 20 °C / Inert atmosphere; Molecular sieve
2: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere; Autoclave
3: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: methanol; dichloromethane / 4 h / 20 °C / Molecular sieve; Inert atmosphere
2: C43H30BF15N2O2RuS; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Autoclave
3: hydrogenchloride / acetic acid methyl ester / 6 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: methanol; dichloromethane / 4 h / 20 °C / Molecular sieve; Inert atmosphere
2: C43H30BF15N2O2RuS; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Autoclave
3: hydrogenchloride / acetic acid methyl ester / 6 h / 20 °C
View Scheme
1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: aluminum (III) chloride / 4 h / 100 °C / Inert atmosphere
2: chiral HPLC / Resolution of racemate
3: methanol; dichloromethane / 96 h / 20 °C / Inert atmosphere; Molecular sieve
4: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere
5: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: aluminum (III) chloride / 4 h / 100 °C / Inert atmosphere
2: chiral HPLC / Resolution of racemate
3: methanol; dichloromethane / 96 h / 20 °C / Inert atmosphere; Molecular sieve
4: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere; Autoclave
5: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: aluminum (III) chloride / 1.5 h / 100 °C / Inert atmosphere
2.1: borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 6 h / 25 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: sodium carbonate / hexane / 0.33 h / -40 °C / Inert atmosphere
4.2: 40 h / -40 °C / Inert atmosphere
5.1: water; sodium sulfite / hexane; ethyl acetate / 12 h / 20 °C / Inert atmosphere
6.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
6.2: 0 - 20 °C / Inert atmosphere
7.1: hydrogen / methanol; dichloromethane; water / 5 h / 20 °C / Inert atmosphere
8.1: hydrogenchloride / diethyl ether / 20 °C / Inert atmosphere
View Scheme
(4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-ylidene)methylamine
261776-41-4

(4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-ylidene)methylamine

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: RuBArF(p-cymene)(R,R)-MsDPEN; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere
2: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: [RuBArF(p-cymene)(S,S)-MsDPEN]; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Inert atmosphere
2: hydrogenchloride / ethyl acetate / 6 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: C43H30BF15N2O2RuS; hydrogen / 1,2-dichloro-ethane / 10 h / 40 °C / 38002.6 Torr / Autoclave
2: hydrogenchloride / acetic acid methyl ester / 6 h / 20 °C
View Scheme
cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine
267884-85-5

cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethyl acetate at 20℃; for 6h; Inert atmosphere; optical yield given as %ee;500 mg
With hydrogenchloride In acetic acid methyl ester at 20℃; for 6h;500 mg
(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ol
167026-37-1

(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ol

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
1.2: 0 - 20 °C / Inert atmosphere
2.1: sodium carbonate / hexane / 0.33 h / -40 °C / Inert atmosphere
2.2: 40 h / -40 °C / Inert atmosphere
3.1: water; sodium sulfite / hexane; ethyl acetate / 12 h / 20 °C / Inert atmosphere
4.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
4.2: 0 - 20 °C / Inert atmosphere
5.1: hydrogen / methanol; dichloromethane; water / 5 h / 20 °C / Inert atmosphere
6.1: hydrogenchloride / diethyl ether / 20 °C / Inert atmosphere
View Scheme
(1S,4S)-1-(benzyloxy)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene
1346228-87-2

(1S,4S)-1-(benzyloxy)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium carbonate / hexane / 0.33 h / -40 °C / Inert atmosphere
1.2: 40 h / -40 °C / Inert atmosphere
2.1: water; sodium sulfite / hexane; ethyl acetate / 12 h / 20 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: hydrogen / methanol; dichloromethane; water / 5 h / 20 °C / Inert atmosphere
5.1: hydrogenchloride / diethyl ether / 20 °C / Inert atmosphere
View Scheme
benzyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate
1346228-88-3

benzyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
1.2: 0 - 20 °C / Inert atmosphere
2.1: hydrogen / methanol; dichloromethane; water / 5 h / 20 °C / Inert atmosphere
3.1: hydrogenchloride / diethyl ether / 20 °C / Inert atmosphere
View Scheme
benzyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl(methyl)carbamate
1346228-89-4

benzyl (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl(methyl)carbamate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / methanol; dichloromethane; water / 5 h / 20 °C / Inert atmosphere
2: hydrogenchloride / diethyl ether / 20 °C / Inert atmosphere
View Scheme
sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Sertraline
79617-96-2

Sertraline

Conditions
ConditionsYield
With sodium hydroxide In water; toluene for 0.25h; pH=> 10;93%
With sodium hydroxide In water; ethyl acetate77%
With ammonium hydroxide In water pH=10;
With sodium hydroxide In water
With potassium carbonate In water at 20℃;10.9 g
carbonochloridic acid, chloromethyl ester
22128-62-7

carbonochloridic acid, chloromethyl ester

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

chloromethyl ((1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)(methyl)carbamate

chloromethyl ((1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)(methyl)carbamate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 4.5h;88%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine
267884-85-5

cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2.33333h; Inert atmosphere;86%
sertraline hydrochloride
79559-97-0

sertraline hydrochloride

Cis-(1S)-N-methyl-7-chlorosulphonyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrogen sulphate

Cis-(1S)-N-methyl-7-chlorosulphonyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine hydrogen sulphate

Conditions
ConditionsYield
With chlorosulfonic acid; trifluoroacetic acid at 20℃; for 16h;72%
1-(1,3-bis(palmitoyloxy)propan-2-yl) 10-(4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl) decanedioate

1-(1,3-bis(palmitoyloxy)propan-2-yl) 10-(4-((((4-nitrophenoxy)carbonyl)oxy)methyl)phenyl) decanedioate

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

1-(1,3-bis(palmitoyloxy)propan-2-yl) 10-(4-(((((1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)(methyl)carbamoyl)oxy)methyl)phenyl) decanedioate

1-(1,3-bis(palmitoyloxy)propan-2-yl) 10-(4-(((((1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)(methyl)carbamoyl)oxy)methyl)phenyl) decanedioate

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;65%
3-(2-((6-((1,3-bis(palmitoyloxy)propan-2-yl)oxy)-6-oxohexanoyl)oxy)-4,6-dimethylphenyl)-3-methylbutanoic acid

3-(2-((6-((1,3-bis(palmitoyloxy)propan-2-yl)oxy)-6-oxohexanoyl)oxy)-4,6-dimethylphenyl)-3-methylbutanoic acid

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

1,3-bis(palmitoyloxy)propan-2-yl (2-(4-(((1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)(methyl)amino)-2-methyl-4-oxobutan-2-yl)-3,5-dimethylphenyl) adipate

1,3-bis(palmitoyloxy)propan-2-yl (2-(4-(((1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)(methyl)amino)-2-methyl-4-oxobutan-2-yl)-3,5-dimethylphenyl) adipate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;61%
sertraline hydrochloride
79559-97-0

sertraline hydrochloride

UK-373911

UK-373911

Conditions
ConditionsYield
Stage #1: sertraline hydrochloride With chlorosulfonic acid In dichloromethane at 20℃; for 0.5h;
Stage #2: With thionyl chloride In dichloromethane at 20℃; for 16h;
Stage #3: With ammonia; trifluoroacetic acid more than 3 stages;		58%
sertraline hydrochloride
79559-97-0

sertraline hydrochloride

(1S-cis )-4-(3,4-dichlorophenyl)-7-iodo-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine
291306-20-2

(1S-cis )-4-(3,4-dichlorophenyl)-7-iodo-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine

Conditions
ConditionsYield
Stage #1: sertraline hydrochloride With N-iodo-succinimide; trifluorormethanesulfonic acid In dichloromethane at 0℃; for 41h;
Stage #2: With sodium hydroxide In dichloromethane; water		35%
Stage #1: sertraline hydrochloride With N-iodo-succinimide; trifluorormethanesulfonic acid In dichloromethane at 0℃; for 41h;
Stage #2: With sodium hydroxide In dichloromethane; water		35%
sertraline hydrochloride
79559-97-0

sertraline hydrochloride

C17H16Cl2IN*HI

C17H16Cl2IN*HI

Conditions
ConditionsYield
With iodine In ethanol
acetic acid
64-19-7

acetic acid

sertraline hydrochloride
79559-97-0

sertraline hydrochloride

sertraline hydrochloride acetic acid solvate
620168-87-8, 820211-78-7

sertraline hydrochloride acetic acid solvate

Conditions
ConditionsYield
at 20 - 60℃; for 16h;
sertraline hydrochloride
79559-97-0

sertraline hydrochloride

A

Cis-(1S)-N-methyl-7-(nitro)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

Cis-(1S)-N-methyl-7-(nitro)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine

B

C17H16Cl2N2O2

C17H16Cl2N2O2

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; potassium nitrate; trifluoroacetic acid at 0℃; for 1.5h;

Sertraline hydrochloride Specification

The Sertraline hydrochloride with the cas number 79559-97-0, is also called (1)(1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthylamine hydrochloride; (2) Adjuvin ; (3) Atruline ; (4) Gladem ; (5) Serad ; (6) Sertraline HCl ; (7) Sertraline hydrochloride ; (8) Tatig ; (9) Tresleen ; (10) Zoloft ; (11)1-Naphthalenamine, 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-, hydrochloride, (1S-cis)- . It belongs to the following product categories:(1)Pharmaceutical Intermediates; (2)Active PharmaceuticalIngredients; (3)APIs; (4)Inhibitors; (5)Intermediates & Fine Chemicals; (6)Pharmaceuticals; (7)Serotonin receptor 

Properties of Sertraline hydrochloride are: (1)ACD/LogP: 4.81 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 1.77 ; (4)ACD/LogD (pH 7.4): 2.77 ; (5)ACD/BCF (pH 5.5): 2.41 ; (6)ACD/BCF (pH 7.4): 24.52 ; (7)ACD/KOC (pH 5.5): 8.89 ; (8)ACD/KOC (pH 7.4): 90.64 ; (9)#H bond acceptors: 1 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 2 ; (12)Polar Surface Area: 3.24Å2 ; (13)Flash Point: 205.6 °C ; (14)Enthalpy of Vaporization: 66.96 kJ/mol; (15)Boiling Point: 416.3 °C at 760 mmHg ; (16)Vapour Pressure: 3.85E-07 mmHg at 25°C

The Sertraline hydrochloride appears to be white or white-like crystalline powder. The Sertraline hydrochloride is mainly used for treatment with depression and obsessive-compulsive disorder. Usage and dosage: The usual dose is 50mg, once a day. Dose can be increased according to patient's condition within weeks, the maximum amount can reach 200mg/day. Please pay attention to using this medicine, because it can cause the following adverse effects: slight xerocheilia, nausea, indigestion, liquid stools and diarrhea. A few patients may show tremor, sweating, defering male ejaculation. Serum transaminase occasionally asymptomatically increase.

You can still convert the following datas into molecular structure :
1. SMILES: Cl.Clc1ccc(cc1Cl)[C@H]3c2c(cccc2)[C@@H](NC)CC3
2. InChI: InChI=1/C17H17Cl2N.ClH/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11;/h2-6,8,10,12,17,20H,7,9H2,1H3;1H/t12-,17-;/m0./s1

The Sertraline hydrochloride toxic data can be showed in the following sheet.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 2857ug/kg (2.857mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

GASTROINTESTINAL: NAUSEA OR VOMITING

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER		 Shinkei Seishin Yakuri. Neuropsychopharmacology. Vol. 19, Pg. 395, 1997.
mouse LDLo intraperitoneal 56mg/kg (56mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: FOOD INTAKE (ANIMAL)		 Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
mouse LDLo oral 336mg/kg (336mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: FOOD INTAKE (ANIMAL)		 Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
rat LDLo intraperitoneal 56mg/kg (56mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: FOOD INTAKE (ANIMAL)		 Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
rat LDLo oral 840mg/kg (840mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS		 Drug and Chemical Toxicology. Vol. 21, Pg. 163, 1998.
women TDLo oral 7mg/kg/2W-I (7mg/kg) BEHAVIORAL: HEADACHE

MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER		 Journal of Clinical Psychiatry. Vol. 54, Pg. 432, 1993.
women TDLo oral 7mg/kg/7D-I (7mg/kg) BEHAVIORAL: EXCITEMENT Journal of Clinical Psychiatry. Vol. 54, Pg. 321, 1993.

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