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118864-75-8

(1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline

CAS: 118864-75-8

Molecular Formula: C15H15N

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118864-75-8 - Names and Identifiers

Name (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline
Synonyms Solifenacin Impurity A
(S)-1-1-Phenyl-1,2,3,4-Tetrahy
Solifenacin Related Compound 11
Solifenacin(YM905) intermediate 10
Solifenacin Succinate interMediate F
(S)-1-PHENYL-1,2,3,4-TRTROHYDROISOQUINOLINE
(S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline
(S)-1,2,3,4-TETRAHYDRO-1-PHENYLISOQUINOLINE
(1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline
(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline
(S)-1,2,3,4- four-1- phenylhydrogenisoquinoline
(S)-1-(Phenyl-d5)-1,2,3,4-tetrahydroisoquinoline
(1S)-1,2,3,4-Tetrahydro-1-(phenyl-d5)isoquinoline
(1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline in stock Factory
(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline, Solifenacin intermediate
CAS 118864-75-8
EINECS 1806241-263-5
InChI InChI=1/C15H15N/c1-2-7-13(8-3-1)15-14-9-5-4-6-12(14)10-11-16-15/h1-9,15-16H,10-11H2/t15-/m0/s1

118864-75-8 - Physico-chemical Properties

Molecular FormulaC15H15N
Molar Mass209.29
Density1.065
Melting Point80-82°C
Boling Point338°C
Flash Point167°C
Solubility Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
Vapor Presure9.87E-05mmHg at 25°C
AppearanceWhite solid
ColorWhite to Off-White
pKa8.91±0.40(Predicted)
Storage Conditionunder inert gas (nitrogen or Argon) at 2–8 °C
Refractive Index1.589
MDLMFCD08692036

118864-75-8 - Reference Information

Application (S)-1-phenyl -1,2,3, 4-tetrahydroisoquinoline can be used to prepare Sofenasin. Solifenacin succinate (SolifenacinSuccinate),CAS No. 242478-38-2, chemical name 1-azabicyclo [2.2.2] octane -8-yl-(1S)-1-phenyl -3, 4-dihydro-1H-isoquinoline -2-formate succinate, is a selective muscarinic M3 receptor antagonist developed by Japan Astellas Company. It was first listed in Holland, Germany, Britain and Denmark in 2004 and in China in 2009, so far, it has been marketed in more than 50 countries and regions around the world, and has become an important drug for the treatment of overactive bladder (OAB) in Europe, the United States and Japan, and has been recommended by many authoritative organizations and guidelines. The preparation is as follows: (S)-1-phenyl -1,2,3, 4-tetrahydroisoquinoline (I) is condensed with triphosgene under the condition of organic base (weak base) to obtain (S)-1-phenyl -3, 4-dihydro-1 H-isoquinoline -2-formyl chloride (II), compound II can not be separated, direct heating under organic base catalysis by a one-pot method, condensation reaction with (R)-3-quinine cycloalcohol to obtain solinasine (III), and then salt with succinic acid to obtain solinasine succinate (IV).
synthesis add 10mL of methanol solution of 1-phenyl -1,2,3,4-tetrahydroisoquinoline (racemate raw material) 2750mg (chemical purity 87.4 mass%,11.5mmol) to the solution formed by L-tartaric acid 1726mg(11.5mmol,1 equivalent) and methanol 10mL, and cool to 5 ℃, precipitation of crystals. Stir for 1 h, and then filter under reduced pressure to remove the precipitated (R)-1-phenyl -1,2,3, 4-tetrahydroisoquinoline/L-tartaric acid salt (R-type tartrate crystal). The optical purity of (S)-1-phenyl -1,2,3, 4-tetrahydroisoquinoline S-type raw material in the obtained mother liquor was determined as 83% e.e.. Add 20mL of water to it and distill under reduced pressure to remove methanol. Add 30% by mass sodium hydroxide aqueous solution to the obtained solution (19.65g) until pH 12, and precipitate crystals. Cool to 5 ℃, stir for 30 minutes, then filter the crystals under reduced pressure, wash with 20mL of water, and dry in vacuum to obtain white crystals of (S)-1-phenyl -1,2,3, 4-tetrahydroisoquinoline (S-type raw material) (S)-1-phenyl -1,2,3, 4-tetrahydroisoquinoline (1092mg, chemical purity 93% by mass, 4.83mmol, yield 42 mol%, optical purity 82% e.e.).
Last Update：2024-04-09 21:04:16
118864-75-8
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