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[ CAS No. 1134-47-0 ] {[proInfo.proName]}

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Chemical Structure| 1134-47-0
Chemical Structure| 1134-47-0
Structure of 1134-47-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1134-47-0 ]

CAS No. :1134-47-0 MDL No. :MFCD00055143
Formula : C10H12ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KPYSYYIEGFHWSV-UHFFFAOYSA-N
M.W : 213.66 Pubchem ID :2284
Synonyms :
(±)-Baclofen
Chemical Name :4-Amino-3-(4-chlorophenyl)butanoic acid

Calculated chemistry of [ 1134-47-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 55.32
TPSA : 63.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : -0.96
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 1.96
Log Po/w (SILICOS-IT) : 1.87
Consensus Log Po/w : 1.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.61
Solubility : 52.1 mg/ml ; 0.244 mol/l
Class : Very soluble
Log S (Ali) : 0.12
Solubility : 279.0 mg/ml ; 1.3 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -2.89
Solubility : 0.273 mg/ml ; 0.00128 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 1134-47-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P301+P310+P330-P405-P501 UN#:2811
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1134-47-0 ]

* 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 [ 1134-47-0 ]

[ 1134-47-0 ] Synthesis Path-Downstream   1~94

  • 2
  • [ 111-87-5 ]
  • [ 1134-47-0 ]
  • [ 111-85-3 ]
  • [ 131403-01-5 ]
  • 3
  • [ 1134-47-0 ]
  • [ 22518-27-0 ]
YieldReaction ConditionsOperation in experiment
90% With aluminum oxide; In toluene; for 16h;Heating / reflux; To a solution of 4-amino-3-(4-chlorophenyl)-butanoic acid (baclofen) (1.0 g, 4.7 mmol) in toluene (80 mL) was added neutral alumina (1.4 g, 14 mmol). The mixture was heated to reflux for 16 h, then cooled to room temperature and filtered. The filtrate was evaporated to give the title compound as a white solid (0.82 g, 90%). Exact mass calculated for CioH10ClNO: 195.1, found: LCMS m/z = 196.1 [M+H]+.
In toluene;Distilation; The solution of ethyl 3-(4-chlorophenyl)-4-nitrobutanoate (2.33 g) in acetic acid (18 ml) was stirred vigorously while iron powder (5.7 g) was added. The suspension was strred at reflux temperature for 1.5 h. The resulting thick slurry was pored into a mixture of cone. HCI (30 ml) and ice (30 g). The aqueous layer was extracted with dichloromethane (2 x 50 ml) and the combined organic layers washed with water and dried (sodium sulfate). After evaporation of the solvent the oily residue was distilled with toluene to remove acetic acid whereupon crystallisation took place. The crude was washed with diethyl ether (3 x 2 ml) and dried in vacuo to afford 4-(4-chlorophenyl)-2-pyrrolidone (0.86 g) as colourless crystals.
Step 1: 4-(4-Chloro-phenyl)-pvrrolidin-2-one[00759] To Baclofen (1.Og, 4.7mmol) in CH2Cl2 (2OmL) was added thionyl chloride (0.38mL, 5.2mmol), and the reaction was stirred for 10 minutes. Dsopropylethylamine (1.5mL) was added, and the mixture was worked-up to give the title compound.
  • 4
  • [ 1134-47-0 ]
  • [ 70-34-8 ]
  • γ-2,4-Dinitrophenylamino-β-(p-chlorophenyl)butyric acid [ No CAS ]
  • 5
  • [ 1134-47-0 ]
  • [ 71-36-3 ]
  • baclofen n-butyl ester hydrochloride [ No CAS ]
  • 7
  • [ 1943-83-5 ]
  • [ 1134-47-0 ]
  • [ 213407-00-2 ]
  • 9
  • [ 110-78-1 ]
  • [ 1134-47-0 ]
  • 3-(-chlorophenyl)-4-(3-propylureido)butyric acid [ No CAS ]
  • 10
  • [ 1134-47-0 ]
  • [ 103-71-9 ]
  • 3-(4-chlorophenyl)-4-(3-phenylureido)butyric acid [ No CAS ]
  • 12
  • [ 1134-47-0 ]
  • [ 1795-48-8 ]
  • 3-(4-chlorophenyl)-4-(3-isopropylureido)butyric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Preferably, the compound having agonistic or partially agonistic affinity to a GABAB receptor is any one of the following compounds: 4-amino-3-(4-chlorophenyl)butanoic acid (baclofen), (3-aminopropyl)methylphosphinic acid, (3-amino-2-hydroxypropyl)methylphosphinic acid, 4-aminobutanoic acid (GABA), (3-amino-2-(4-chlorophenyl)propyl)sulfinic acid, (3-aminopropyl)(difluoromethyl)phosphinic acid, (3-amino-2-oxo-propyl)methyl phosphinic acid, 4-amino-3-(5-chlorothien-2-yl)butanoic acid, (3-aminopropyl)phosphonous acid.
By "GABAergic derivatives", is meant in particular the following compounds (optionally in the form of pharmaceutically acceptable salts): gabapentin; baclofen; or pregabalin.
Examples of 4-aminobutanoic acid GABAB receptor ligands include: 4-amino-3-(4-chlorophenyl)butanoic acid (baclofen); (3R)-4-amino-3-(4-chlorophenyl)butanoic acid (R-baclofen); 4-amino-3-(2-chlorophenyl)butanoic acid; 4-amino-3-(4-fluorophenyl)butanoic acid; (3R)-4-amino-3-(4-fluorophenyl)butanoic acid; 4-amino-3-hydroxybutanoic acid; 4-amino-3-(4-chlorophenyl)-3-hydroxyphenylbutanoic acid; 4-amino-3-(thien-2-yl)butanoic acid; 4-amino-3-(5-chlorothien-2-yl)butanoic acid; ...
, wherein the compound is selected from the group consisting of: 4-aminobutanoic acid (GABA), 4-amino-3-(4-chlorophenyl)butanoic acid (baclofen), 4-amino-3-phenylbutanoic acid, 4-amino-3-hydroxybutanoic acid, 4-amino-3-(4-chlorophenyl)-3-hydroxyphenylbutanoic acid, 4-amino-3-(thien-2-yl)butanoic acid, 4-amino-3-(5-chlorothien-2-yl)butanoic acid, 4-amino-3-(5-bromothien-2-yl)butanoic acid, 4-amino-3-(5-methylthien-2-yl)butanoic acid, ...
Preferably, the compound having agonistic or partially agonistic affinity to a GABAB receptor is any one of the following compounds: 4-amino-3-(4-chlorophenyl)butanoic acid (baclofen), (3-aminopropyl)methylphosphinic acid, (3-amino-2-hydroxypropyl)methylphosphinic acid,

  • 15
  • [ 1134-47-0 ]
  • [ 40993-10-0 ]
  • 3-(4-chloro-phenyl)-4-(3,5-dinitro-benzoylamino)-butyric acid [ No CAS ]
  • 16
  • [ 1134-47-0 ]
  • [ 407-25-0 ]
  • [ 22518-27-0 ]
  • [ 229014-55-5 ]
  • 17
  • [ 71-23-8 ]
  • [ 1134-47-0 ]
  • baclofen 1-propyl ester hydrochloride [ No CAS ]
  • 18
  • [ 64-17-5 ]
  • [ 1134-47-0 ]
  • ethyl 4-amino-3-(4-chlorophenyl)butanoate hydrochloride [ No CAS ]
  • 19
  • [ 1134-47-0 ]
  • [ 67-63-0 ]
  • baclofen 2-propyl ester hydrochloride [ No CAS ]
  • 20
  • [ 927207-26-9 ]
  • [ 1134-47-0 ]
  • 21
  • [ 24424-99-5 ]
  • [ 1134-47-0 ]
  • [ 78131-30-3 ]
YieldReaction ConditionsOperation in experiment
84% BOC2O (5.32 g, 24.41 mmol, 1 eq) was added to a stirred solution of Baclofen (5.20 g, 24.41 mmol) and NaOH IM (73 ml) in water (73 ml) and 1,4- dioxane (73 ml) at O C. After stirring for 4 h at room temperature, a 10 % aqueous solution o citric acid was added until pH 3. The formed white solid was filtered, washed with water (50 ml) and dried. The pure acid 33 was obtained without further purification (6.43 g, 20.56 mmol, 84 %), mp 139-141 "C1H NMR (400 MHz, CD3OD) delta 1.37 (9H5 s), 2.50 (IH, dd, J 8.8, 15.2 Hz)5 2.66 (IH5 dd5 J 5.0, 15.4 Hz)5 3.12-3.27 (3H, m), 7.22 (2H, d, J 8.4 Hz)5 7.27 (2H, d, J 8.4 Hz)
  • 22
  • [ 1134-47-0 ]
  • 6-(4-chlorophenyl)perhydro-1,3-diazepine-2,4-dione [ No CAS ]
  • 25
  • [ 1134-47-0 ]
  • [ 229014-56-6 ]
  • 26
  • [ 1134-47-0 ]
  • [ 229014-57-7 ]
  • 27
  • [ 1134-47-0 ]
  • 5-chloro-3-oxoindan-1-ylmethylammonium chloride [ No CAS ]
  • 28
  • [ 1134-47-0 ]
  • 4-(4-chlorophenyl)-2-oxo-pyrrolidine-1-carboxylic acid ethylamide [ No CAS ]
  • 29
  • [ 1134-47-0 ]
  • [ 41216-03-9 ]
  • 30
  • [ 1134-47-0 ]
  • (RS)-4-<N-(tert-butyloxycarbonyl)amino>-3-(4-chlorophenyl)butane [ No CAS ]
  • 31
  • [ 1134-47-0 ]
  • [ 229182-24-5 ]
  • 32
  • [ 1134-47-0 ]
  • [ 229182-23-4 ]
  • 33
  • [ 1134-47-0 ]
  • [ 229182-25-6 ]
  • 34
  • [ 1134-47-0 ]
  • (RS)-5-amino-4-(4-chlorophenyl)pentanoic acid hydrochloride [ No CAS ]
  • 35
  • [ 1134-47-0 ]
  • 4-(4-chlorophenyl)-2-oxo-pyrrolidine-1-carboxylic acid amide [ No CAS ]
  • 36
  • [ 1134-47-0 ]
  • 6-(4-Chloro-phenyl)-3-ethyl-[1,3]diazepane-2,4-dione [ No CAS ]
  • 37
  • [ 1134-47-0 ]
  • 6-(4-Chloro-phenyl)-3-isopropyl-[1,3]diazepane-2,4-dione [ No CAS ]
  • 38
  • [ 1134-47-0 ]
  • 6-(4-Chloro-phenyl)-3-propyl-[1,3]diazepane-2,4-dione [ No CAS ]
  • 39
  • [ 1134-47-0 ]
  • [ 213407-05-7 ]
  • 40
  • [ 1134-47-0 ]
  • 6-(4-Chloro-phenyl)-3-phenyl-[1,3]diazepane-2,4-dione [ No CAS ]
  • 41
  • [ 1134-47-0 ]
  • 6-(4-Chloro-phenyl)-3-(2-pyrrolidin-1-yl-ethyl)-[1,3]diazepane-2,4-dione [ No CAS ]
  • 42
  • [ 1134-47-0 ]
  • 6-(4-Chloro-phenyl)-3-(2-morpholin-4-yl-ethyl)-[1,3]diazepane-2,4-dione [ No CAS ]
  • 43
  • [ 1134-47-0 ]
  • [ 187870-40-2 ]
  • 44
  • [ 1134-47-0 ]
  • [ 1027508-88-8 ]
  • 45
  • [ 1134-47-0 ]
  • (6S,8S)-6-(4-Chloro-phenyl)-5,6,7,8-tetrahydro-indolizin-8-ol [ No CAS ]
  • 46
  • [ 1134-47-0 ]
  • [ 187870-30-0 ]
  • 47
  • [ 1134-47-0 ]
  • [ 187870-71-9 ]
  • 48
  • [ 1134-47-0 ]
  • [ 1027402-62-5 ]
  • 49
  • [ 1134-47-0 ]
  • 1-[6-(4-Chloro-phenyl)-6,7-dihydro-5H-indolizin-8-ylidene]-pyrrolidinium; perchlorate [ No CAS ]
  • 50
  • [ 1134-47-0 ]
  • 8-amino-6-(4-chlorophenyl)-5,6,7,8-tetrahydroindolizine [ No CAS ]
  • 51
  • [ 1134-47-0 ]
  • Benzyl-[(6R,8R)-6-(4-chloro-phenyl)-5,6,7,8-tetrahydro-indolizin-8-yl]-amine [ No CAS ]
  • 52
  • [ 1134-47-0 ]
  • 3-(4-Chloro-phenyl)-4-{2-[2-(4-chloro-phenyl)-benzooxazol-5-yl]-propionylamino}-butyric acid butyl ester [ No CAS ]
  • 53
  • [ 1134-47-0 ]
  • 1-acetyl-4-(4-chlorophenyl)-pyrrolid-2-one [ No CAS ]
  • 54
  • [ 1134-47-0 ]
  • 4-(4-chlorophenyl)-1-(4-methoxybenzoyl)-pyrrolid-2-one [ No CAS ]
  • 55
  • [ 1134-47-0 ]
  • 4-(4-chlorophenyl)-1-(4-methoxybenzenosulfonyl)-pyrrolid-2-one [ No CAS ]
  • 56
  • [ 1134-47-0 ]
  • 4-(4-chlorophenyl)-1-(3,4,5-trimethoxybenzoyl)-pyrrolid-2-one [ No CAS ]
  • 57
  • [ 1134-47-0 ]
  • [ 120418-62-4 ]
  • 60
  • [ 99-91-2 ]
  • 6-<<i>p</i>-tolylimino-methyl>-benzo<1.3>dioxol-5-ylamine [ No CAS ]
  • [ 1134-47-0 ]
  • 61
  • [ 81187-93-1 ]
  • [ 1134-47-0 ]
  • 62
  • [ 81187-91-9 ]
  • [ 1134-47-0 ]
  • 63
  • [ 81187-90-8 ]
  • [ 1134-47-0 ]
  • 64
  • [ 1134-47-0 ]
  • [ 136552-08-4 ]
  • [ 181819-28-3 ]
YieldReaction ConditionsOperation in experiment
palladium-carbon; In ethanol; water; Step A 4-guinidino-3-p-chlorophenylbutyric acid hydrochloride was made using the method of Example 1 Step E, substituting 222.2 g of 4-amino-3-p-chlorophenylbutyric acid (RBI) for 5-aminovaleric acid. This product was reduced with 10% Pd/C in 50% EtOH/H2 O under 50 psi H2 overnight to yield 4-guanidino-3phenylbutyric acid hydrochloride.
palladium-carbon; In ethanol; water; Step A 4-guinidino-3-p-chlorophenylbutyric acid hydrochloride was made using the method of Example 1 Step E, substituting 222.2 g of 4-amino-3-p-chlorophenylbutyric acid (RBI) for 5-aminovaleric acid. This product was reduced with 10% Pd/C in 50% EtOH/H2 O under 50 psi H2 overnight to yield 4-guanidino-3-phenylbutyric acid hydrochloride.
  • 65
  • [ 1134-47-0 ]
  • [ 7693-46-1 ]
  • [ 1057667-83-0 ]
YieldReaction ConditionsOperation in experiment
With chloro-trimethyl-silane; triethylamine; In tetrahydrofuran; at 0 - 30℃; for 6h; 312.0 ml (2.458 mol) of trimethylchlorosilane was added slowly to the suspension of 350.0 gm (1.638 mol) of baclofen in THF (1400 ml) in presence of 387.0 ml (2.78 mol) of triethylamine at 0-5 C over 1.5 hrs and maintained at 0-50C for 30 minutes. Solution of 347.0 gm (1.721 mol) of 4-nitrophenylchlorofomate in THF (1050 ml) was added to <n="44"/>the above reaction mixture between 0-50C over 1.5 hrs and maintained at 25-30C for 2.5hrs. Reaction mixture was cooled to below 10C and added DM water (1750 ml) followed by IN HCl (1750 ml) and separated organic layer at room temperature. The aqueous layer was saturated with sodium chloride (600 gm) and extracted with THF (2x875 ml). Combined organic layer was dried over anhydrous sodium sulfate and solvent distilled under vacuum. Resulting solid was dissolved in IPA (1900 ml) at 75- 800C and cooled to 0-5C and product was filtered, washed with chilled IPA (400 ml), suck dried and finally dried at 50-550C under vacuum to get 3-(4-chlorophenyl)-4-[(4- nitrophenoxy)carbonyl]amino } butanoic acid.
  • 66
  • [ 136897-39-7 ]
  • [ 1134-47-0 ]
  • C27H42ClNO3 [ No CAS ]
  • 67
  • [ 112-16-3 ]
  • [ 1134-47-0 ]
  • [ 1073838-93-3 ]
  • 68
  • [ 764-85-2 ]
  • [ 1134-47-0 ]
  • [ 1073838-91-1 ]
  • 69
  • [ 38460-95-6 ]
  • [ 1134-47-0 ]
  • [ 1073838-95-5 ]
  • 70
  • [ 17746-05-3 ]
  • [ 1134-47-0 ]
  • [ 1073838-92-2 ]
  • 71
  • [ 1134-47-0 ]
  • [ 75-36-5 ]
  • [ 1073838-88-6 ]
  • 72
  • [ 1134-47-0 ]
  • [ 111-64-8 ]
  • [ 1073838-90-0 ]
  • 73
  • [ 1134-47-0 ]
  • [ 112-64-1 ]
  • [ 1073838-94-4 ]
  • 74
  • [ 1134-47-0 ]
  • [ 103-80-0 ]
  • [ 1073838-97-7 ]
  • 75
  • ethyl rac β-[(aminomethyl)-4-chlorophenyl]-propancarboxylate [ No CAS ]
  • [ 1134-47-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water;Cooling with ice; The solution of ethyl 3-(4-chlorophenyl)-4-nitrobutanoate (2.33 g) in acetic acid (18 ml) was stirred vigorously while iron powder (5.7 g) was added. The suspension was strred at reflux temperature for 1.5 h. The resulting thick slurry was pored into a mixture of cone. HCI (30 ml) and ice (30 g). The aqueous layer was extracted with dichloromethane (2 x 50 ml) and the combined organic layers washed with water and dried (sodium sulfate). After evaporation of the solvent the oily residue was distilled with toluene to remove acetic acid whereupon crystallisation took place. The crude was washed with diethyl ether (3 x 2 ml) and dried in vacuo to afford 4-(4-chlorophenyl)-2-pyrrolidone (0.86 g) as colourless crystals.
  • 76
  • [ 1134-47-0 ]
  • [ 100-52-7 ]
  • [ 1347999-79-4 ]
  • 77
  • [ 1134-47-0 ]
  • [ 69308-37-8 ]
  • (S)-(+)-baclofen [ No CAS ]
YieldReaction ConditionsOperation in experiment
With chiral stationary phase including isopropyl-functionalized CF6; In methanol; acetic acid; triethylamine; acetonitrile; at 20℃;Purification / work up; In addition to the foregoing, numerous other chromatographic separations using a column bonded with a CSP including a derivatized cyclofructan residue were carried out. Tables 5-9 list some additional examples of chromatographic separations using a column bonded with a CSP of the present invention. AU examples of chromatographic separations using columns bonded with CSPs of the present invention were carried out using the following experimental conditions and procedures.|0132| The high performance liquid chromatography (HPLC) column packing system was composed of an air driven fluid pump (HASKEL, DSTV- 122), an air compressor, a pressure regulator, a low pressure gauge, two high-pressure gauges (10,000 and 6,000 psi), a slurry chamber, check valves, and tubings. The CSPs were slurry packed into a 25 cm x 0.46 cm (inner diameter, I. D.) stainless steel column.|0133| The HPLC system was an Agilent 1 100 system (Agilent Technologies, Palo Alto,CA), which consisted of a diode array detector, an autosampler, a binary pump, a temperature- controlled column chamber, and Chemstation software. All chiral analytes were dissolved in ethanol, methanol, or other appropriate mobile phases, as indicated. For the LC analysis, the injection volume and flow rate were 5 muL and 1 mL/min, respectively. Separations were carried out at room temperature (~20 0C) if not specified otherwise. The wavelengths of UV detection were 195, 200, 210, and 254 nm. The mobile phase was degassed by ultrasonication under vacuum for 5 min. Each sample was analyzed in duplicate. Three operation modes (the normal phase mode, polar organic mode, and reversed phase mode) were tested, unless indicated otherwise. In the normal phase mode, heptane with ethanol or isopropanol was used as the mobile phase. In some cases, trifluoroacetic acid (TFA) was used as an additive, as indicated. The mobile phase of the polar organic mode was composed of acetonitrile/methanol and small amounts of acetic acid and triethylamine. Water/acetonitrile or acetonitrile/acetate buffer (20 mM, pH = 4.1 ) was used as the mobile phase in the reversed-phase mode.|0134| Two different supercritical fluid chromatographic instruments were used. One was a Berger SFC unit with an FCM 1200 flow control module, a TCM 2100 thermal column module, a dual pump control module, and a column selection valve. The flow rate was 4 mL/min. The cosolvent was composed of methanol/ethanol/isopropanol = 1 : 1 : 1 and 0.2% diethylamine (DEA). The gradient mobile phase composition was 5% cosolvent hold during 0- 0.6 min, 5-60% during 0.6-4.3 min, 60% hold during 4.3-6.3 min, 60%-5% during 6.3-6.9 min, and 5% hold during 6.9-8.0 min. The other SFC system was a Jasco (MD, USA) system comprised of an autosampler unit (AS-2059-SF Plus), a dual pump module (PU-2086 Plus), a column thermostat module (CO-2060 Plus), a UV/Vis detector (UV-2075 Plus), and a back pressure regulator module (SCH-Vch-BP). Unless otherwise specified, the mobile phase was composed of CCVmethanol (0.1 % TFA or 0.1% diethylamine). The flow rate was 3 mL/min.|0135| For the calculations of chromatographic data, the "dead time" to was determined by the peak of the refractive index change due to the sample solvent or determined by injecting l ,3,5-tri-/e/-/-butylbenzene in the normal phase mode.
  • 78
  • [ 1134-47-0 ]
  • [ 1455091-23-2 ]
  • [ 1455087-60-1 ]
YieldReaction ConditionsOperation in experiment
28 mg With sodium methylate; In 2-methoxy-ethanol; for 3h;Reflux; Methyl l-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate (70 mg, 0.22 mmol), (±)- baclofen (134 mg, 1.10 mmol, Sigma-Aldrich) and sodium methoxide (53 mg, 0.98 mmol) were suspended in 2-methoxyethanol (7 mL). The resulting mixture was heated to reflux for 3 hours and then cooled to room temperature. The solvent was removed in vacuo and the residue was dissolved in H20 (20 mL) and EtOAc (20 mL). To the stirred mixture was added 1 N hydrochloric acid until pH was 1. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO/t, concentrated, and purified by flash chromatography (0-50% EtOAc/hexanes with 0.5% formic acid) to give the title compound in 28 mg. MS: (-) m/z 499.95 (M-l).
  • 79
  • 3-chloro-4-(4-chlorophenyl)-5-hydroxyfuran-2(5H)-one [ No CAS ]
  • [ 1134-47-0 ]
  • 80
  • 3-chloro-4-(4-chlorophenyl)-1-(2,4-dimethoxybenzyl)-1H-pyrrol-2(5H)-one [ No CAS ]
  • [ 1134-47-0 ]
  • 81
  • 3-chloro-4-(4-chlorophenyl)-1H-pyrrol-2(5H)-one [ No CAS ]
  • [ 1134-47-0 ]
  • 82
  • [ 1679-18-1 ]
  • [ 1134-47-0 ]
  • 83
  • [ 1134-47-0 ]
  • N-(4-chloro-6-piperidinyl[1,3,5]triazine-2-yl)-L-phenylalanine [ No CAS ]
  • C27H31ClN6O4 [ No CAS ]
  • C27H31ClN6O4 [ No CAS ]
  • 88
  • Baclofen hydrochloride [ No CAS ]
  • [ 1134-47-0 ]
YieldReaction ConditionsOperation in experiment
41% With ammonium hydroxide; In methanol; at 60℃; for 2h;pH 6.9 - 7; The baclofen was obtained by neutralization of baclofen hydrochlorideusing NH3/H2O. For this purpose, methanol solutionof the baclofen hydrochloride was heated to 60 C and 12%NH3/H2O was dropped carefully to the reaction mixture to pH6.9e7.0 and then the reaction mixture was intensively stirred for2 h. Crystallizationwas conducted from methanol. Very thin needlecrystals were filtered and washed with cold water. The product wasdried at 60 C. Yield of synthesis was 41%. Despite repeated attemptsit appeared very difficult to obtain really good qualitycrystals for X-ray diffraction analysis.
  • 89
  • (E)-3-(4-chlorophenyl)-3-cyanoacrylic acid [ No CAS ]
  • [ 1134-47-0 ]
YieldReaction ConditionsOperation in experiment
70% With ammonia; hydrogen; In water; at 25 - 30℃; for 6h; Example-3: Preparation of Baclofen (I) Charged compound 3-(4-chlorophenyl)-3-cyanopropanoic acid (A) (100 g) and aqueous ammonia (600 mL) in a hydrogenation reactor, followed by the addition of Raney nickel (10 g). The reaction mixture was stirred under hydrogen pressure (10 kg) at temperature about 25-30 C for 5 hours. The reaction mixture was filtered and the excess ammonia was distilled off. The aqueous layer was treated with 50 % sodium hydroxide solution (50 mL) and was further treated with ethylenediaminetetra acetic acid disodium salt dihydrate (5 g). The aqueous layer was extracted with MDC (50 mL) and the separated aqueous layer was acidified using dilute hydrochloric acid solution (pH 6.5-7) followed by the addition of iso-propanol (200 mL). The desired precipitated product was isolated by filtration with a yield of 70 % and a purity of 99 % (HPLC).
  • 90
  • [ 118-48-9 ]
  • [ 1134-47-0 ]
  • [ 100-52-7 ]
  • 3-(4-chlorophenyl)-4-(1,2-dihydro-4-oxo-2-phenylquinazolin-3(4H)-yl)butanoic acid [ No CAS ]
  • C24H21ClN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With propyl sulfonic acid-functionalized SBA-15; In neat (no solvent); at 110℃; for 2h; General procedure: To the mixture of isatoic anhydride (160 mg, 1 mmol),gabapentin or baclofen (1 mmol), and aromatic aldehyde(1 mmol), SBA-Pr-SO3H (0.02 g) was added, and then itwas stirred at 110 C for an appropriate period of time.After completion of the reaction, the mixture of productswas dissolved in hot EtOH to remove the heterogeneouscatalyst. Then, the solvent was evaporated and extractedusing EtOAc and then washed with water. Some productscontained a mixture of two diastereoisomers. Further purificationwas done using crystallization in water/EtOH (1:4).
  • 91
  • [ 118-48-9 ]
  • [ 1134-47-0 ]
  • [ 123-11-5 ]
  • 3-(4-chlorophenyl)-4-(1,2-dihydro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl)butanoic acid [ No CAS ]
  • C25H23ClN2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With propyl sulfonic acid-functionalized SBA-15; In neat (no solvent); at 110℃; for 2h; General procedure: To the mixture of isatoic anhydride (160 mg, 1 mmol),gabapentin or baclofen (1 mmol), and aromatic aldehyde(1 mmol), SBA-Pr-SO3H (0.02 g) was added, and then itwas stirred at 110 C for an appropriate period of time.After completion of the reaction, the mixture of productswas dissolved in hot EtOH to remove the heterogeneouscatalyst. Then, the solvent was evaporated and extractedusing EtOAc and then washed with water. Some productscontained a mixture of two diastereoisomers. Further purificationwas done using crystallization in water/EtOH (1:4).
  • 92
  • [ 118-48-9 ]
  • [ 1134-47-0 ]
  • [ 459-57-4 ]
  • 3-(4-chlorophenyl)-4-(2-(4-fluorophenyl)-1,2-dihydro-4-oxoquinazolin-3(4H)-yl)butanoic acid [ No CAS ]
  • C24H20ClFN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With propyl sulfonic acid-functionalized SBA-15; In neat (no solvent); at 110℃; for 2h; General procedure: To the mixture of isatoic anhydride (160 mg, 1 mmol),gabapentin or baclofen (1 mmol), and aromatic aldehyde(1 mmol), SBA-Pr-SO3H (0.02 g) was added, and then itwas stirred at 110 C for an appropriate period of time.After completion of the reaction, the mixture of productswas dissolved in hot EtOH to remove the heterogeneouscatalyst. Then, the solvent was evaporated and extractedusing EtOAc and then washed with water. Some productscontained a mixture of two diastereoisomers. Further purificationwas done using crystallization in water/EtOH (1:4).
  • 93
  • [ 118-48-9 ]
  • [ 1134-47-0 ]
  • [ 104-87-0 ]
  • 3-(4-chlorophenyl)-4-(1,2-dihydro-4-oxo-2-p-tolylquinazolin-3(4H)-yl)butanoic acid [ No CAS ]
  • C25H23ClN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With propyl sulfonic acid-functionalized SBA-15; In neat (no solvent); at 110℃; for 2h; General procedure: To the mixture of isatoic anhydride (160 mg, 1 mmol),gabapentin or baclofen (1 mmol), and aromatic aldehyde(1 mmol), SBA-Pr-SO3H (0.02 g) was added, and then itwas stirred at 110 C for an appropriate period of time.After completion of the reaction, the mixture of productswas dissolved in hot EtOH to remove the heterogeneouscatalyst. Then, the solvent was evaporated and extractedusing EtOAc and then washed with water. Some productscontained a mixture of two diastereoisomers. Further purificationwas done using crystallization in water/EtOH (1:4).
  • 94
  • [ 118-48-9 ]
  • [ 1134-47-0 ]
  • [ 1122-91-4 ]
  • C24H20BrClN2O3 [ No CAS ]
  • 3-(4-chlorophenyl)-4-(1,2-dihydro-2-(4-bromophenyl)-4-oxoquinazolin-3(4H)-yl)butanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With propyl sulfonic acid-functionalized SBA-15; In neat (no solvent); at 110℃; for 2h; General procedure: To the mixture of isatoic anhydride (160 mg, 1 mmol),gabapentin or baclofen (1 mmol), and aromatic aldehyde(1 mmol), SBA-Pr-SO3H (0.02 g) was added, and then itwas stirred at 110 C for an appropriate period of time.After completion of the reaction, the mixture of productswas dissolved in hot EtOH to remove the heterogeneouscatalyst. Then, the solvent was evaporated and extractedusing EtOAc and then washed with water. Some productscontained a mixture of two diastereoisomers. Further purificationwas done using crystallization in water/EtOH (1:4).
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[ 1134-47-0 ]

Chemical Structure| 28311-31-1

A1638717[ 28311-31-1 ]

Baclofen hydrochloride

Reason: Free-salt