CAS No.124937-52-6,Tolterodine tartrate Suppliers

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Basic Information

Molecular Structure:
CAS No.:	124937-52-6
Name:	Tolterodine tartrate
Article Data:	13

Formula:	C₂₂H₃₁NO^.C₄H₆O₆
Molecular Weight:	475.582
Synonyms:	Phenol, 2-(3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-methyl-, (R)-, (R-(R,R))-2,3-dihydroxybutanedioate (1:1) (salt);Detrol (TN);Phenol, 2-((1R)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-methyl-, (2R,3R)-2,3-dihydroxybutanedioate (1:1) (salt);(2R,3R)-2,3-dihydroxybutanedioic acid; 2-[(1R)-3-(dipropan-2-ylamino)-1-phenyl-propyl]-4-methyl-phenol;Detrusitol (TN);Detrol;Tolterodine tartrate (JAN/USAN);Detrusitol;Tolterodine tartrate [USAN];Detrol LA;L-(+)- Tolterodine Tartrate;Tolterodine L-Tartrate;Tolterodine-L-Tartrate;(+)-R)-2-{A-[2-(Diisopropylamino)Ethyl]Benzyl}-P-Cresol Tartrate;
EINECS:	620-503-4
Density:	1.003 g/cm³
Melting Point:	205-210 °C
Boiling Point:	442.2 °C at 760 mmHg
Flash Point:	192.1 °C
Solubility:	soluble in water
Appearance:	white-to-off-white crystalline powder
Hazard Symbols:	Xi
Risk Codes:	20/21/22
Safety:	36/37
PSA:	138.53000
LogP:	3.21880

Synthetic route

: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride With sodium carbonate; sodium hydroxide In dichloromethane; water at 20℃; for 1h; Stage #2: L-Tartaric acid In methanol; acetone for 1h; Reflux;	88%
Stage #1: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride With sodium carbonate; sodium hydroxide In dichloromethane; water at 0 - 20℃; for 1h; Stage #2: L-Tartaric acid In methanol; acetone at 0℃; for 2h; Reflux;	30%
Stage #1: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride With sodium hydroxide In dichloromethane; water at 25 - 35℃; for 0.0833333 - 0.166667h; Stage #2: L-Tartaric acid In methanol; dichloromethane; water; acetonitrile at 0 - 35℃; for 6.58333 - 13h; Heating / reflux;
Stage #1: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride With sodium carbonate; sodium hydroxide In dichloromethane; water Stage #2: L-Tartaric acid In ethanol at 0 - 70℃;	n/a

: 837376-36-0
3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: 3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide With sodium hydroxide In dichloromethane; water Stage #2: L-Tartaric acid In ethanol at 60 - 85℃;	39%

: 897314-72-6
(+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: (+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 5 - 40℃; for 6h; Cooling with ice; Stage #2: L-Tartaric acid In ethanol at 0 - 70℃; Reflux;	37%

N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine: N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
In ethanol at 60 - 85℃;	18%
In ethanol at 0 - 80℃; for 5h; Resolution of racemate;
In methanol; acetone; toluene at 20 - 60℃; for 12.5h; Resolution of racemate;	n/a
In ethanol Product distribution / selectivity;

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: tolterodine hydrobromide With potassium hydroxide In water; ethyl acetate for 0.25 - 0.5h; Stage #2: L-Tartaric acid In ethanol; ethyl acetate at 0℃; for 5 - 17h; Product distribution / selectivity;

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
In ethanol at 25 - 30℃; for 0.5h; Product distribution / selectivity; Resolution of racemate;

: 897314-72-6
(+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide

: 87-69-4
L-Tartaric acid

A: 873551-03-2
(S)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate

B: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Stage #1: (+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 70℃; for 6.08333h; Inert atmosphere; Cooling with ice; Stage #2: With sodium hydroxide In acetone; toluene at 40 - 60℃; for 0.25h; Stage #3: L-Tartaric acid In methanol at 0℃; Product distribution / selectivity; Reflux;	A n/a B n/a
Stage #1: (+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 5 - 40℃; for 6h; Cooling with ice; Stage #2: L-Tartaric acid In isopropyl alcohol at 20 - 75℃; for 3.5h; Product distribution / selectivity;	A n/a B n/a

...Expand

: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine hydrochloride

: 87-69-4
L-Tartaric acid

A: 873551-03-2
(S)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate

B: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
In ethanol at 0 - 70℃;	A n/a B n/a

...Expand

: 1043911-42-7
N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propylamine L-tartrate

: 87-69-4
L-Tartaric acid

: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
In water; isopropyl alcohol at 20 - 65℃; Purification / work up; Resolution of racemate; Reflux;	n/a

: N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-2-propenamide

A: 873551-03-2
(S)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate

B: 124937-52-6
tolterodine tartrate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen / 5%-palladium/activated carbon / water; 2-methyltetrahydrofuran / 2.5 h / 55 °C / 750.08 Torr 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 6 h / 5 - 40 °C / Cooling with ice 2.2: 3.5 h / 20 - 75 °C View Scheme
Multi-step reaction with 3 steps 1.1: hydrogen / 5%-palladium/activated carbon / water; 2-methyltetrahydrofuran / 2.5 h / 55 °C / 750.08 Torr 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 6 h / 5 - 40 °C / Cooling with ice 2.2: 20 - 60 °C 3.1: ethanol / 0 - 70 °C View Scheme

Raw Materials

94-02-0

87-69-4

Total:181 Page 1 of 5 1 2 3 4 5 Next>>

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Chemistry

Molecular Structure of Tolterodine tartrate (CAS NO.124937-52-6):

IUPAC Name: (2R,3R)-2,3-dihydroxybutanedioic acid; 2-[(1S)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol
Empirical Formula: C₂₆H₃₇NO₇
Molecular Weight: 475.5745
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 8
Polar Surface Area: 12.47Å²
Flash Point: 192.1 °C
Enthalpy of Vaporization: 72.66 kJ/mol
Boiling Point: 442.2 °C at 760 mmHg
Vapour Pressure: 1.97E-08 mmHg at 25°C
Melting point: 205-210°C
InChI
InChI=1/C22H31NO.C4H6O6/c1-16(2)23(17(3)4)14-13-20(19-9-7-6-8-10-19)21-15-18(5)11-12-22(21)24;5-1(3(7)8)2(6)4(9)10/h6-12,15-17,20,24H,13-14H2,1-5H3;1-2,5-6H,(H,7,8)(H,9,10)/t20-;1-,2-/m01/s1
Smiles
c1([C@H](c2ccccc2)CCN(C(C)C)C(C)C)c(ccc(c1)C)O.C([C@@H]([C@H](C(=O)O)O)O)(=O)O
Product Categories: Active Pharmaceutical Ingredients; Medicine intermediate;APIs; In treatment of urinary incontinence; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Tolterodine

Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.

Standards and Recommendations

oxybutynin (M3 and M1 selective, but more so in the parotid than in the bladder) as tolterodine targets the bladder more than other areas of the body. This means that less drug needs to be given daily (due to efficient targeting of the bladder) and so there are fewer side effects.Tolterodine, although it acts on all types of receptors, has fewer side effects than other antimuscarinics eg. Tolterodine acts on M1, M2, M3, M4 and M5 subtypes of muscarinic receptors whereas modern antimuscarinic treatments for overactive bladder only act on M3 receptors making them more selective.

Specification

Tolterodine tartrate , with CAS number of 124937-52-6, can be called 2-((1R)-3-(Bis(1-methylethyl)amino)-1-phenylpropyl)-4-methylphenol (2R,3R)-2,3-dihydroxybutanedioate (1:1) (salt) ; 2,3-Dihydroxybutandisäure--2-{(1R)-3-[bis(1-methylethyl)amino]-1-phenylpropyl}-4-methylbenzolol(1:1) ; 2-[(1R)-3-(Diisopropylamino)-1-phenylpropyl]-4-methylphenol 2,3-dihydroxysuccinate (1:1) ; acide 2,3-dihydroxybutanedioïque - 2-{(1R)-3-[bis(1-méthyléthyl)amino]-1-phénylpropyl}-4-méthylphénol (1:1) . Tolterodine tartrate (CAS NO.124937-52-6) is used to treat urinary incontinence.Tolterodine is an antimuscarinic drug.