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[ CAS No. 5586-73-2 ]

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Chemical Structure| 5586-73-2
Chemical Structure| 5586-73-2
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Product Details of [ 5586-73-2 ]

CAS No. :5586-73-2 MDL No. :MFCD00008202
Formula : C15H17N Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :211.30 g/mol Pubchem ID :-
Synonyms :

Safety of [ 5586-73-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5586-73-2 ]

  • Downstream synthetic route of [ 5586-73-2 ]

[ 5586-73-2 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 3531-24-6 ]
  • [ 5586-73-2 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; acetic acid; platinum Hydrogenation;
With sodium hydroxide; ammonia; hydrogen In methanol
Multi-step reaction with 2 steps 1: amalgamated aluminium 2: platinum; acetic acid; H2SO4 / Hydrogenation
  • 2
  • [ 2286-54-6 ]
  • [ 5586-73-2 ]
  • 4
  • [ 18592-13-7 ]
  • [ 5586-73-2 ]
  • [ 73541-50-1 ]
  • 5
  • [ 5586-73-2 ]
  • [ 79-04-9 ]
  • [ 137075-21-9 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In dichloromethane; at 0℃; for 0.75h; 1 g (4.73 mmol, 1 eq.) of 3,3-diphenylpropylamine and 732 μL (5.21 mmol, 1.1 eq.) of triethylamine are diluted in 30 mL of DCM at 0 C under argon. 300 μL (3.77 mmol, 0.8 eq.) of chloroacetyl chloride are added dropwise. White fumes form then gradually dissipate. The mixture is stirred for 45 min. at 0 C, the solution becomes red. A dilute HCl solution is added then the aqueous phase is extracted with DCM. The organic phase is washed once with water then once with brine, dried over MgSO4, filtered and concentrated. The product is obtained in the form of an oil (m = 1.36 g, yield = 100%).1H NMR(400 MHz, CDCl3): ppm 2.24 (q, 2H, CH2), 3.21 (q, 2H, CH2), 3.82-3.92 (m, 3H, CH+CH2), 6.37-6.50 (m, IH, NH), 7.06-7.25 (m, 1OH, aromatic H). MS: 288.09+ (M+H)+, 329.11+ (M+H+CH3CN)+ <n="158"/>TLC: Rf= 0.73 (eluent: DCM/MeOH 95/5)
With triethylamine; In tetrahydrofuran; at 0℃; for 2h; Method D: <n="138"/>Synthesis of 2-CMoro-N-("3.3-diphenyl-propylVacetamide:25 g (0.118 mol, 1 eq) of 3,3-diphenyl-propylamine and 20.7 mL (0.147 mol, 1.25 eq) of triethylamine were diluted in 250 mL of THF at 0 C, under argon. 9.85 mL (0.124 mol, 1.05 eq) of chloroacetyl chloride were added dropwise. White fumes formed then gradually dissipated. The mixture was stirred for 2 h at 0 C, the solution became red and a white precipitate formed. The precipitate was filtered then washed several times with EtOAc. The organic phase was extracted with dilute HCl solution, with water then with brine, dried over MgSO4, filtered and concentrated. The product was obtained as a yellow solid (m = 32 g, yield = 91%).1H NMR (400 MHz, CDCl3): δ 2.24 (q, 2H, CH2), 3.21 (q, 2H, CH2), 3.82-3.92 (m, 3H, CH+CH2), 6.37-6.50 (m, IH, NH), 7.06-7.25 (m, 1OH, aromatic H). MS (ES+): 288.09+ (M+H)+, 329.11+ (M+H+CH3CN)+
  • 6
  • [ 5586-73-2 ]
  • [ 122-48-5 ]
  • [ 6154-79-6 ]
  • 7
  • [ 558-42-9 ]
  • [ 5586-73-2 ]
  • 1-(3,3-diphenylpropyl)amino-2-methyl-2-propanol [ No CAS ]
  • 8
  • [ 5586-73-2 ]
  • [ 207557-35-5 ]
  • 1-[(3,3-diphenyl)propylamino]acetyl-2-cyano-(S)-pyrrolidine [ No CAS ]
  • 9
  • [ 89424-83-9 ]
  • [ 5586-73-2 ]
  • N-[(3,4-methylenedioxy)benzylidene]-N-(3,3-diphenylpropyl)amine [ No CAS ]
  • 10
  • [ 5586-73-2 ]
  • [ 35310-75-9 ]
  • [1-(3-Bromo-4-methoxy-phenyl)-eth-(E)-ylidene]-(3,3-diphenyl-propyl)-amine [ No CAS ]
  • 11
  • [ 5586-73-2 ]
  • [ 35310-75-9 ]
  • N-(3,3-diphenylpropyl)-1-(3-bromo-4-methoxyphenyl)ethylamine [ No CAS ]
  • 12
  • [ 5586-73-2 ]
  • [ 110661-91-1 ]
  • [ 1002566-64-4 ]
YieldReaction ConditionsOperation in experiment
52.6% With potassium carbonate; In acetonitrile;Heating / reflux; EXAMPLE 67 (R)-l-(3<3-diphenvIpropyI)-3-(4-(4-(methylsuIfonamido)phenyl)thiazol-2-vI)-l-(4-oxo-4-(piperidin-3-ylamino)butvI)urea; Step 1: Tert-butyl 3-bromopropionate 1 (0.5 mL, 3.0 mmol) was dissolved in 100 mL of dry acetonitrile. To this solution was added potassium carbonate (0.415g, 3.0 mmol) and 3,3-diphenylpropylamine 2. The reaction mixture was refluxed overnight. The mixture was then allowed to cool to room temperature and was concentrated in vacuo. The crude residue obtained was dissolved in ethyl acetate (45 mL) and washed with saturated aqueous ammonium chloride solution and then with brine. The organics were dried over magnesium sulfate, filtered and concentrated to obtain the crude product as a clear oil. This product was purified by column chromatography on silica using 89:9:l/DCM:MeOH:ammonium hydroxide as eluent. Fractions containing product were combined and concentrated in vacuo to obtain 3 as a white solid (0.54g, 52.6% yield).
  • 13
  • [ 4530-20-5 ]
  • [ 5586-73-2 ]
  • [ 1002567-00-1 ]
YieldReaction ConditionsOperation in experiment
90% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h; Synthesis of [2-(3.3-Diphenyl-propylamino)-ethyll-carbamic acid tert-butyl ester:15 g of 3,3-diphenyl-propylamine (71.1 mmol, 1 eq) and 13.7 g of N-Boc-Glycine (78.2 mmol, 1.1 eq) were diluted in 100 mL of dry DCM. 10.6 g of HOBt (78.2 mmol, 1.1 eq) and 15 g of EDCHCl (78.2 mmol, 1.1 eq) were added to the solution. The reaction mixture was stirred for 16 h at room temperature, under argon, before addition of water. The aqueous phase was extracted several times with DCM, the organics were washed with <n="125"/>brine, dried over MgSO4, filtered then concentrated. The crude product was purified by flash chromatography over silica gel (DCM/ MeOH: 98/ 2 to 96/ 4) to give 23.6 g of the desired amide intermediate [β^-diphenyl-propylcarbamoyty-methylj-carbamic acid tert- butyl ester (90% yield).12 g of this amide intermediate (32.5 mmol, 1 eq) were solubilized in 100 mL of dry THF, under argon. After cooling the solution to O0C, 71.6 mL Of LiAlH4 (1 M in THF, 71.6 mmol, 2.2 eq) were added dropwise to the solution. The reaction mixture was stirred for 16 h at room temperature, then cooled to 0C before slow addition of water. After stirring for 1 h at room temperature, the mixture was filtered to get rid of aluminium salts and the solid was washed several times with EtOAc. The aqueous phase was extracted several times with EtOAc, then the organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified with flash chromatography over silica gel (DCM/ MeOH: 98/ 2 to 90/ 10) to give 8.6 g of the desired secondary amine [2-(3,3-diphenyl-propylamino)-ethyl]-carbamic acid tert-butyl ester (70% yield).1H NMR (400 MHz, DMSO): δ 7.28 (m, 8H, aromatic H), 7.15 (m, 2H, aromatic H), 6.68 (t, IH, NH), 4.02 (t, IH, CH), 2.93 (q, 2H, CH2), 2.45 (t, 2H, CH2), 2.38 (t, 2H, CH2), 2.11 (q, 2H, CH2), 1.36 (s, 9H, 3xCH3). MS (ES+): 355.2+ (M+H)+
  • 14
  • [ 314033-91-5 ]
  • [ 5586-73-2 ]
  • [ 314033-93-7 ]
YieldReaction ConditionsOperation in experiment
80% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 15h; 4 Synthesis of 2-(2-chloroethoxy) methyl-4-(3-chlorophenyl-5-(3,3-diphenylpropylcarbamoyl)-2-methyl-1,4-dihydropyridine-3-carboxylic acid (2-cyanoethyl) ester: 250 mg (0.560 mmol) of 2-(2-chloroethoxy) methyl-4-(3-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid 5-(2-cyanoethyl) ester, 110 mg (0.570 mmol) of WSC hydrochloride and 120 mg (0.570 mmol) of 3,3-diphenylpropylamine were stirred at room temperature for 15 hours in 4 ml of dichloromethane. After evaporating dichloromethane under reduced pressure, 0.1 N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound. Yield: 280 mg (0.450 mmol) (80%) MS (ESI, m/z) 632 (M+H)+ 1H-NMR (CDCl3): 2.14 (2H, s), 2.67 (2H, t), 3.10 (2H, m), 3.72 (2H, m), 3.83 (2H, m), 4.31 (2H, m), 4.73 (1H, s), 4.82 (2H, s), 5.56 (1H, t), 7.11-7.26 (15H, m).
With hydrogenchloride; In dichloromethane; 4) Synthesis of 6-(2-chloroethoxy) methyl-4-(3-chlorophenyl)-5-(3,3-diphenylpropylcarbamoyl)-2-methyl- 1,4-dihydropyridine-3-carboxylic acid (2-cyanoethyl) ester: 250 mg (0.560 mmol) of 2-(2-chloroethoxy) methyl-4-(3-chlorophenyl)-6-methyl- 1,4-dihydropyridine-3,5-dicarboxylic acid 5-(2-cyanoethyl) ester, 110 mg (0.570 mmol) of WSC hydrochloride and 120 mg (0.570 mmol) of 3,3-diphenylpropylamine were stirred at room temperature for 15 hours in 4 ml of dichloromethane. After evaporating dichloromethane under reduced pressure, 0.1 N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane / ethyl acetate = 1/1) to obtain the title compound. Yield: 280 mg (0.450 mmol) (80%) MS (ESI, m/z) 632 (M+H)+ 1H-NMR (CDCl3): 2.14 (2H, s), 2.67 (2H, t), 3.10 (2H, m), 3.72 (2H, m), 3.83 (2H, m), 4.31 (2H, m), 4.73 (1H, s), 4.82 (2H, s), 5.56 (1H, t), 7.11-7.26 (15H, m).
  • 15
  • [ 215119-93-0 ]
  • [ 5586-73-2 ]
  • 4-(3-chlorophenyl)-2,6-dimethyl-5-(3,3-diphenylpropylcarbamoyl)-1,4-dihydropyridine-3-carboxylic acid 2-cyanoethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; 2 Synthesis of 4-(3-chlorophenyl)-2,6-dimethyl-5-(3,3-diphenylpropylcarbamoyl)-1,4-dihydropyridine-3-dicarboxylic acid 2-cyanoethyl ester: 219 mg (0.610 mmol) of 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid mono (2-cyanoethyl) ester, 138 mg (0.720 mmol) of WSC hydrochloride, 201 mg (0.950 mmol) of 3,3-diphenylpropylamine and 20.0 mg (0.160 mmol) of 4-dimethylaminopyridine were stirred at room temperature overnight in 10 ml of dichloromethane. 2 N hydrochloric acid was added and the reaction mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound. Yield: 280 mg (0.510 mmol) (83%) MS (ESI, m/z) 554 (M+H)+ 1H-NMR (CDCl3): 2.05-2.23 (2H, m), 2.21 (3H, s), 2.32 (3H, s), 2.64 (2H, t), 3.06-3.22 (2H, m), 3.72 (1H, t), 4.20-4.35 (2H, m), 4.73 (1H, s), 5.31 (1H, t), 5.58 91H, s), 7.09-7.30 (14H, m).
83.3% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; 1) Synthesis of 2-cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-(3,3-diphenylpropylcarbamoyl)-1,4-dihydropyridine-3-carboxylate 219 mg (0.61 mmol) of mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, 138 mg (0.72 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 201 mg (0.95 mmol) of 3,3-diphenylpropylamine and 20 mg (0.16 mmol) of 4-dimethylaminopyridine were stirred in 10 ml of dichloromethane at room temperature overnight. 2 N hydrochloric acid was added to the reaction mixture. After the extraction with dichloromethane, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/1) to obtain the title compound. Yield: 280mg (0.51 mmol) (83.3%) MS (ESI, m/z) 554 (M+H)+ 1H-NMR (CDCl3): 2.05-2.23 (2H, m), 2.21 (3H, s), 2.32 (3H, s), 2.64 (2H, t), 3.06-3.22 (2H, m), 3.72 (1H, t), 4.20-4.35 (2H, m), 4.73 (1H, s), 5.31 (1H, t), 5.58 (1H, s), 7.09-7.30 (14H, m)
  • 16
  • [ 5586-73-2 ]
  • [ 94790-37-1 ]
  • [ 141595-76-8 ]
  • [ 248921-61-1 ]
YieldReaction ConditionsOperation in experiment
0.63 g (72%) With N-ethyl-N,N-diisopropylamine; In diethyl ether; N,N-dimethyl-formamide; EXAMPLE 5 Preparation of (S)-Azepane-1-carboxylic acid [1-(3,3-diphenyl-propylcarbamoyl)-3-methyl-butyl]-amide (S)-2-[(Azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid (0.51 g, 2.0 mmol, Example 1, Step B) was dissolved in dry DMF (5 mL) under nitrogen atmosphere and cooled to 0 C. in an ice-water bath. To this solution were added, in succession, N,N-diisopropylethylamine (0.68 mL, 3.9 mmol) and solid O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate (0.74 g, 2.0 mmol). The resulting reaction mixture was stirred at that temperature for 30 minutes; 3,3-diphenylpropylamine (0.41 g, 1.9 mmol, Aldrich, Milwaukee, Wis.) was then added. After additional 30 minutes stirring at 0 C., reaction mixture was mixed with 60 mL of diethyl ether; the resulting mixture was successively washed with 5% aqueous HCl solution, brine, saturated aqueous NaHCO3 solution, brine, and was dried over Na2SO4. The solution was concentrated in vacuo, a white solid was obtained. Recrystallization from EtOAc-hexanes afforded 0.63 g (72%) of the pure titled compound as a white solid; mp 144-145 C. APCI-MS m/z 450.3 (MH+).
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