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33286-22-5

Basic Information
CAS No.: 33286-22-5
Name: 1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,hydrochloride (1:1), (2S,3S)-
Molecular Structure:
Molecular Structure of 33286-22-5 (1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,hydrochloride (1:1), (2S,3S)-)
Formula: C22H26N2O4S.HCl
Molecular Weight: 451.02
Synonyms: 1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,monohydrochloride, (2S,3S)- (9CI);1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,monohydrochloride, (2S-cis)-;(+)-Diltiazem hydrochloride;(2S,3S)-(+)-cis-Diltiazem hydrochloride;(S,S)-Diltiazem hydrochloride;Adizem;Altiazem;Anginyl;Blocalcin 60;Britiazim;CRD401;Calcicard;Cardizem SR;Dilacor XR;Diladel;Dilcardia;Dilgard;Dilzene;d-cis-3-Acetoxy-2,3-dihydro-5-[2-(dimethylamino)ethyl]-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-onehydrochloride;d-cis-Diltiazem hydrochloride;
EINECS: 251-443-3
Density: 1.26g/cm3
Melting Point: 212-214 ºC
Boiling Point: 594.4 ºC at 760 mmHg
Flash Point: 313.3 ºC
Solubility: Soluble in water
Appearance: Fine needles
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-40-36/37/38
Safety: 36-45-36/37-26
Transport Information: UN 3249
PSA: 84.38000
LogP: 4.23550
Synthetic route
42399-40-6

O-desacetyldiltiazem

108-24-7

acetic anhydride

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
Stage #1: O-desacetyldiltiazem; acetic anhydride With dmap; triethylamine In dichloromethane for 3h; Heating / reflux;
Stage #2: With hydrogenchloride In methanol pH=2;
92%
With hydrogenchloride In ethanol; butanone at 90℃; for 1h;80%
With dmap In dichloromethane for 3h; Heating; Yield given;
75472-91-2

(2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride

108-24-7

acetic anhydride

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
Stage #1: (2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride; acetic anhydride With dmap; triethylamine In dichloromethane
Stage #2: With hydrogenchloride In methanol pH=2;
92%
With pyridine; dmap
108-22-5

Isopropenyl acetate

75472-91-2

(2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
With methanesulfonic acid In chloroform for 0.75h; Heating;88.8%
2419-67-2, 24470-83-5, 41564-61-8

(E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 70 percent / urea hydrogen peroxide, DBU, immobilised poly-L-leucine / tetrahydrofuran / 28 h
2: 84 percent / MCPBA, KF / CH2Cl2 / 24 h
3: 90 percent / toluene / 17 h / Heating
4: 94 percent / xylene / 216 h / Heating
5: K2CO3 / ethyl acetate
6: pyridine, DMAP
View Scheme
42399-49-5

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3 / ethyl acetate
2: pyridine, DMAP
View Scheme
Multi-step reaction with 2 steps
1: 67 percent / NaH / dimethylformamide; paraffin; diethyl ether / 3 h / 70 °C
2: 80 percent / 2.) HCl / butan-2-one; ethanol / 1 h / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: 88.2 percent / K2CO3 / H2O; ethyl acetate / 5 h / Heating
2: DMAP / CH2Cl2 / 3 h / Heating
View Scheme
123-11-5

4-methoxy-benzaldehyde

(+-)-2-cyano-3-m-tolyl-propionic acid hydrazide

(+-)-2-cyano-3-m-tolyl-propionic acid hydrazide

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 87 percent / NaOMe / methanol / 40 h / Heating
2: 70 percent / urea hydrogen peroxide, DBU, immobilised poly-L-leucine / tetrahydrofuran / 28 h
3: 84 percent / MCPBA, KF / CH2Cl2 / 24 h
4: 90 percent / toluene / 17 h / Heating
5: 94 percent / xylene / 216 h / Heating
6: K2CO3 / ethyl acetate
7: pyridine, DMAP
View Scheme
201804-22-0

tert-butyl (2R,3S)-3-(4-methoxyphenyl)glycidate

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / toluene / 17 h / Heating
2: 94 percent / xylene / 216 h / Heating
3: K2CO3 / ethyl acetate
4: pyridine, DMAP
View Scheme
201804-23-1

(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid tert-butyl ester

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / xylene / 216 h / Heating
2: K2CO3 / ethyl acetate
3: pyridine, DMAP
View Scheme
201804-19-5

1-((2R,3S)-4-methoxyphenyloxiranyl)-2,2-dimethylpropan-1-one

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 84 percent / MCPBA, KF / CH2Cl2 / 24 h
2: 90 percent / toluene / 17 h / Heating
3: 94 percent / xylene / 216 h / Heating
4: K2CO3 / ethyl acetate
5: pyridine, DMAP
View Scheme
42399-48-4

(2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 88 percent / PTSA / xylene / 16 h / Heating
2: 88.2 percent / K2CO3 / H2O; ethyl acetate / 5 h / Heating
3: DMAP / CH2Cl2 / 3 h / Heating
View Scheme
138382-02-2

(αS,βS,1R,2S)-β-<(2-aminophenyl)thio>-α-hydroxy-β-(4-methoxyphenyl)propanoic acid 2-phenylcyclohexyl ester hydrochloride

33286-22-5

diltiazem hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81 percent / 2 N NaOH / ethanol; H2O / 2 h / Heating
2: 88 percent / PTSA / xylene / 16 h / Heating
3: 88.2 percent / K2CO3 / H2O; ethyl acetate / 5 h / Heating
4: DMAP / CH2Cl2 / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 73.2 percent / PTSA / xylene / 16 h / Heating
2: 88.2 percent / K2CO3 / H2O; ethyl acetate / 5 h / Heating
3: DMAP / CH2Cl2 / 3 h / Heating
View Scheme
33286-22-5

diltiazem hydrochloride

5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Conditions
ConditionsYield
With water; hydrogen bromide at 100℃; for 0.5h;96%
33286-22-5

diltiazem hydrochloride

23515-44-8

cis(+)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

Conditions
ConditionsYield
With lithium hydroxide; water In tetrahydrofuran at 160℃; for 0.0833333h; Microwave irradiation;94%
33286-22-5

diltiazem hydrochloride

42399-40-6

O-desacetyldiltiazem

Conditions
ConditionsYield
In water Ambient temperature; Irradiation; decomposition of diltiazem in various solvents;
With sodium chloride at 79.85℃; Kinetics; Thermodynamic data; Activation energy; Further Variations:; Temperatures; relative humidity;
With hydrogenchloride at 39.85℃; pH=0.43; Kinetics; Further Variations:; pH-values; Reagents; Temperatures;
33286-22-5

diltiazem hydrochloride

42399-41-7

diltiazem

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; ethyl acetate
With sodium carbonate In water pH=7.5;
With sodium hydrogencarbonate In water for 0.25h;

C62H68N16O24S4(4-)*4Na(1+)

33286-22-5

diltiazem hydrochloride

C22H26N2O4S*ClH*C62H68N16O24S4(4-)*4Na(1+)

Conditions
ConditionsYield
In aq. phosphate buffer pH=7.4; UV-irradiation;
33286-22-5

diltiazem hydrochloride

diltiazem acetylsalicylate hydrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate / water / pH 7.5
2: diethyl ether / 20 °C
View Scheme
33286-22-5

diltiazem hydrochloride

diltiazem nicotinate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate / water / pH 7.5
2: acetonitrile / 20 °C
View Scheme
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42399-41-7
42399-40-6
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    33286-22-5

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Specification

The Diltiazem HCl, with the CAS registry number 33286-22-5, is also known as (+)-cis-3-(Acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)one monohydrochloride. It belongs to the product categories of Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals; Calcium Channel; Ion Channels; Aromatics; Chiral Reagents; Sulfur & Selenium Compounds. Its EINECS registry number is 251-443-3. This chemical's molecular formula is C22H27ClN2O4S and molecular weight is 450.98. What's more, both its IUPAC name and systematic name are the same which is called [(2S,3S)-5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate hydrochloride. It is used as a calcium channel blocher with vasodilating activity and an antianginal, antihypertensive.

Physical properties about Diltiazem HCl are: (1)ACD/LogP: 3.63; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.76; (4)ACD/LogD (pH 7.4): 2.26; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 14.49; (7)ACD/KOC (pH 5.5): 3.03; (8)ACD/KOC (pH 7.4): 96.24; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 84.38 Å2; (13)Flash Point: 313.3 °C; (14)Enthalpy of Vaporization: 88.6 kJ/mol; (15)Boiling Point: 594.4 °C at 760 mmHg; (16)Vapour Pressure: 4.27E-14 mmHg at 25 °C.

Preparation of Diltiazem HCl: this chemical can be prepared by 2-Acetoxy-propene with (2S,3S)-5-(2-Dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride. This reaction needs reagent methanesulfonic acid, solvent CHCl3 and other condition of heating for 45 min. The yield is 88.8 %.

Diltiazem HCl can be prepared by 2-Acetoxy-propene with (2S,3S)-5-(2-Dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. If swallowed, it's harmful to health. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1) SMILES: Cl.O=C2N(c3c(S[C@@H](c1ccc(OC)cc1)[C@H]2OC(=O)C)cccc3)CCN(C)C
(2) InChI: InChI=1S/C22H26N2O4S.ClH/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3;/h5-12,20-21H,13-14H2,1-4H3;1H/t20-,21+;/m1./s1
(3) InChIKey: HDRXZJPWHTXQRI-BHDTVMLSSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 40mg/kg (40mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 4843, 1987.
man LDLo oral 21mg/kg (21mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Postgraduate Medical Journal. Vol. 69, Pg. 474, 1993.
man TDLo oral 3429ug/kg/2D- (3.429mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Lancet. Vol. 341, Pg. 967, 1993.
man TDLo oral 15420ug/kg/7D (15.42mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Archives of Internal Medicine. Vol. 151, Pg. 1869, 1991.
man TDLo oral 36mg/kg/13D-I (36mg/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)" Gastroenterology. Vol. 88, Pg. 1260, 1985.
mouse LD50 intraperitoneal 177mg/kg (177mg/kg)   Journal of Medicinal Chemistry. Vol. 29, Pg. 820, 1986.
mouse LD50 intravenous 58mg/kg (58mg/kg) BEHAVIORAL: ANTIPSYCHOTIC Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
mouse LD50 oral 508mg/kg (508mg/kg)   Journal of Medicinal Chemistry. Vol. 33, Pg. 2192, 1990.
mouse LD50 subcutaneous 260mg/kg (260mg/kg) BEHAVIORAL: ANTIPSYCHOTIC Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
rat LD50 intravenous 38mg/kg (38mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TETANY
Japan Medical Gazette. Vol. 11(1), Pg. 12, 1974.
rat LD50 oral 560mg/kg (560mg/kg) BEHAVIORAL: ANTIPSYCHOTIC Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
rat LD50 subcutaneous 520mg/kg (520mg/kg) BEHAVIORAL: ANTIPSYCHOTIC Japanese Journal of Pharmacology. Vol. 22, Pg. 467, 1972.
women LDLo oral 120mg/kg (120mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION Human & Experimental Toxicology. Vol. 13, Pg. 161, 1994.
women TDLo oral 7200ug/kg/2D- (7.2mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS
Journal of the Royal Society of Medicine. Vol. 81, Pg. 296, 1988.
women TDLo oral 7200ug/kg (7.2mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS
Journal of the Royal Society of Medicine. Vol. 81, Pg. 296, 1988.
women TDLo oral 8400ug/kg (8.4mg/kg) CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Annals of Emergency Medicine. Vol. 22, Pg. 196, 1993.
women TDLo oral 18mg/kg (18mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 45, 1991.
women TDLo oral 18mg/kg (18mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 45, 1991.
women TDLo oral 19mg/kg (19mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Postgraduate Medical Journal. Vol. 64, Pg. 467, 1988.

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