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[ CAS No. 3644-61-9 ] {[proInfo.proName]}

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Chemical Structure| 3644-61-9
Chemical Structure| 3644-61-9
Structure of 3644-61-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3644-61-9 ]

CAS No. :3644-61-9 MDL No. :MFCD00058211
Formula : C16H24ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :ZBUVYROEHQQAKL-UHFFFAOYSA-N
M.W :281.82 Pubchem ID :92965
Synonyms :
Tolperisone hydrochloride

Calculated chemistry of [ 3644-61-9 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.56
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 86.91
TPSA : 20.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 4.45
Log Po/w (WLOGP) : 3.72
Log Po/w (MLOGP) : 2.94
Log Po/w (SILICOS-IT) : 3.82
Consensus Log Po/w : 2.98

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.36
Solubility : 0.0123 mg/ml ; 0.0000436 mol/l
Class : Moderately soluble
Log S (Ali) : -4.6
Solubility : 0.00715 mg/ml ; 0.0000254 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.3
Solubility : 0.014 mg/ml ; 0.0000497 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 3644-61-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H319-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3644-61-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3644-61-9 ]

[ 3644-61-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 646-06-0 ]
  • [ 5337-93-9 ]
  • [ 6091-44-7 ]
  • Tolperisone hydrochloride [ No CAS ]
  • 2
  • [ 256469-59-7 ]
  • [ 3644-61-9 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen; triethylamine In ethanol for 1.5h;
YieldReaction ConditionsOperation in experiment
In tert-butyl methyl ether; isopropyl alcohol Heating / reflux;
In isopropyl alcohol; butanone Heating / reflux;
  • 4
  • [ 646-06-0 ]
  • [ 5337-93-9 ]
  • [ 6091-44-7 ]
  • [ 158176-60-4 ]
  • [ 756433-31-5 ]
  • Tolperisone hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
6 EXAMPLE 6 EXAMPLE 6 Substitution of equivalent quantities of 1,1-dimethoxy-1-(4-tolyl)-2-methyl-3-chloropropane and piperidine for the 1,1-dimethoxy-1-(4-fluorophenyl)-4-chlorobutane and the 4-(4-chlorophenyl)piperidin-4-ol used in Example 3, and substantial repetition of the procedure detailed therein, affords 1-(4-tolyl)-2-methyl-3-piperidinopropanone hydrochloride, melting at about 176° - 177° C.
  • 6
  • [ CAS Unavailable ]
  • [ 3644-61-9 ]
  • [ 1043449-71-3 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol at 20℃; for 0.5h; 6.1.b b) When equimolar amount of tolperisone hydrochloride is used as an organic amine compound:; A mixture of loxoprofen sodium salt (305 mg, 1 mmol) containing water (12%), tolperisone hydrochloride (282 mg, 1 mmol) and 2-propanol (5 mL) was stirred at room temperature for 30 min. The resulting precipitate was filtered off, and the filtrate was concentrated under reduced pressure to give a loxoprofen-tolperisone salt as a colorless starch syrup-like viscous liquid. This product showed an infrared absorption spectrum similar to that of the above-mentioned a).A mixture of loxoprofen sodium salt (305 mg, 1 mmol) containing water (12%), tolperisone hydrochloride (282 mg, 1 mmol) and 2-propanol (5 mL) was stirred at room temperature for 30 min. The resulting precipitate was filtered off, and the filtrate was concentrated under reduced pressure to give a loxoprofen-tolperisone salt as a colorless starch syrup-like viscous liquid. This product showed an infrared absorption spectrum similar to that of the above-mentioned a).
  • 7
  • [ 3644-61-9 ]
  • [ 62834-89-3 ]
  • [ 1919899-17-4 ]
YieldReaction ConditionsOperation in experiment
1: 66% 2: 15% With water; oxygen; sodium hydroxide In 1,4-dioxane at 80℃; for 24h; Green chemistry; regioselective reaction;
  • 8
  • [ 2377769-86-1 ]
  • [ 3644-61-9 ]
YieldReaction ConditionsOperation in experiment
76% With hydrogenchloride In 1,4-dioxane; water at 20℃; for 2h; 1.3 Step 3: Synthesis of Tolperisone HCl, 2-methyl-3-(piperidin-l-yl)-l-(p-tolyl)propan-l-one hydrochloride A solution of 2-methyl-3-(piperidin-l-yl)-l-(p-tolyl)propan-l-one (150 mg, 0.61 mmol) in 4M HC1 in dioxane (2 mL) and dioxane (3 mL) was stirred at room temperature for 2 hours. The mixture was concentrated under reduced pressure to afford 2-methyl-3-(piperidin-l-yl)-l- (p- tolyl)propan-l-one hydrochloride (130 mg, 76%) as a white solid. LCMS: (ES+): m/z 246.1 [M+H] +. tR = 1.99 min; 1.36 (m, 3H), 1.70-1.85 (m, 4H), 2.04-2.10 (m, 1H), 2.22-2.28 (m, 1H), 2.42-2.46 (m, 4H), 2.73-2.75 (m, 1H), 3.02-3.11 (m, 2H), 3.49-3.52 (m, 1H), 3.77-3.79 (m, 1H), 4.59-4.63 (m, 1H), 7.32 (d, / = 8.0 Hz, 2H), 8.00 (m, 2H), 12.15 (br, 1H).
  • 9
  • [ 3644-61-9 ]
  • [ 109400-86-4 ]
YieldReaction ConditionsOperation in experiment
80% With formic acid; nitromethane; trifluoromethylsulfonic anhydride In acetic acid at 100℃;
  • 10
  • [ 3644-61-9 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
1: 41 % 2: 30 % Stage #1: Tolperisone hydrochloride With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Stage #2: With hydrogenchloride In dichloromethane; water; ethyl acetate Synthesis of Dihydrotolperisone To a stirred suspension of lithium aluminumhydride (80.8 mg, 2.13 mol) prepared in dry tetrahydrofuran (10 mL),tolperisone hydrochloride (300 mg, 1.06 mmol) was added at 0C. After stirringat 0C for 1 hour, complete consumption of tolperisone was confirmed by TLC.The reaction mixture was poured into ice-cold water. The mixture was extractedwith ethyl acetate, and the extract was dried over Na2SO4. Na2SO4 was removedby filtration, and the filtrate was concentrated under reduced pressure to obtain amixture of threo- and erythro-dihydrotolperisone as a colorless oil. The crude material was analyzed by reversed-phase high-performance liquid chromatography(HPLC) with a Cosmosil 5C18-mass spectrometry (MS)-II column (4.6 × 150 mm;Nacalai Tesque, Kyoto, Japan) at a flow rate of 1 mL/min with an isocratic mobilephase of 80% methanol in water with 0.05% triethylamine. Diastereomers 1and 2 appeared at 6.4 and 6.9 minutes, respectively. The crude material wasthen purified by recycling a preparative HPLC system with a Cosmosil 5C18-MS-II column (20 × 250 mm; Nacalai Tesque) at a flow rate of 14 mL/minwith an isocratic mobile phase of 85% methanol in water with 0.05% triethylamine.As HPLC purification was not sufficient to separate the diastereomers,the obtained materials were converted to hydrochloride salts and purified bywashing with an organic solvent. The purified products were analyzed by 1HNMR spectroscopy with a JNM-ESC600 spectrometer (JEOL, Tokyo, Japan). Fractions containing diastereomer 1 as the major compound were concentrated to afford colorless oil. The oil was dissolved in dichloromethane (DCM)(1.0 mL), and 4 M HCl in AcOEt (0.5 mL, 2.0 mmol) was added to the DCMsolution. The mixture was concentrated to obtain a colorless solid. The solidwas washed with DCM:hexane (1:4) to give the hydrochloride salt of dihydrotolperisonediastereomer 1 as a colorless solid (125 mg). The product was characterizedby 1H NMR [(600 MHz, CD3OD) d 7.25 (d, J 5 7.8 Hz, 2H), 7.18(d, J 5 7.8 Hz, 2H), 4.77 (d, J 5 4.2 Hz, 1H), 3.56 (br s, 2H), 3.34-3.25 (m, 3H),3.18 (dd, J 5 13.2, 4.8 Hz, 1H), 3.15-2.78 (m, 3H), 2.46-2.37 (m, 1H),2.33 (s, 3H), 2.10-1.40 (m, 6H), 0.92 (d, J 5 6.6 Hz, 3H)]. The product puritywas 99% (confirmed by quantitative nuclear magnetic resonance using 1,3,5-trimethoxybenzene as the internal standard). Upon taking the purity into account,the yield of diastereomer 1 was 41%. Fractions containing diastereomer 2 as the major compound were concentrated to obtain colorless oil. The oil was dissolved in DCM (1.0 mL), and 4 M HCl inAcOEt (0.5 mL, 2.0 mmol) was added to the DCM solution. The mixture wasconcentrated to obtain a colorless solid. The solid was washed with DCM/hexane(1/4) to obtain the hydrochloride salt of dihydrotolperisone diastereomer 2 as acolorless solid (101 mg). The product was characterized by 1H NMR [(600MHz,CD3OD) d 7.27 (d, J 5 7.8 Hz, 2H), 7.19 (d, J 5 7.8 Hz, 2H), 4.43 (d, J 59.6 Hz, 1H), 3.86 (br d, J 5 12.0 Hz, 1H), 3.55 (br d, J 5 12.0 Hz, 1H), 3.18 (dd,J 5 13.2, 6.0 Hz, 1H), 3.05-2.86 (m, 2H), 2.41-2.30 (m, 1H), 2.33 (s, 3H),2.05-1.50 (m, 6H), 0.72 (d, J 5 6.6 Hz, 3H)]. Product purity was 90% (confirmedby qNMR using 1,3,5-trimethoxybenzene as the internal standard). Upon taking the purity into account, the yield of diastereomer 2 was 30%.
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