Benzenemethanol, α-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, hydrochloride (1:1), (αR)-
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Benzenemethanol, α-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, hydrochloride (1:1), (αR)-
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CAS No:
521284-22-0
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Formula:
C16H20N2O.ClH
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Chemical Name:
Benzenemethanol, α-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, hydrochloride (1:1), (αR)-
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Synonyms:
Benzenemethanol,α-[[[2-(4-aminophenyl)ethyl]amino]methyl]-,hydrochloride (1:1),(αR)-;Benzenemethanol,α-[[[2-(4-aminophenyl)ethyl]amino]methyl]-,monohydrochloride,(αR)-;(R)-2-[2-(4-Aminophenyl)ethylamino]-1-phenylethanol hydrochloride;(R)-2-[(2-(4-Aminophenyl)ethyl)amino]-1-phenylethanol monohydrochloride;(R)-2-[[2-(4-Aminophenyl)ethyl]amino]-1-phenylethanol monohydrochloride;(R)-2-[[2-(4-Aminophenyl)ethyl]amino]-1-phenylethanol hydrochloride;YM 208876;(R)-2-(4-Aminophenethylamino)-1-phenylethanol hydrochloride
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CAS No:
Benzenemethanol, α-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, hydrochloride (1:1), (αR)- Basic Attributes
292.80374
292.134247
1592732-453-0
Safety Information
P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P333+P313, P337+P313, P363, P391, P405, P501
H301
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P333+P313, P337+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 4 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Benzenemethanol, α-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, hydrochloride (1:1), (αR)- Use and Manufacturing
A mixture of (100 g) (R)-2-[2’ -(4-nitrophenyl)ethyl]amino] -1 -phenylethanol monohydroch bride (prepared according to example Ib), methanol (2000 mL) and Raney Nickel (20 g, wet) was stirred under hydrogen pressure (60 psi) for 6 hrs. The reaction solution was filtered, and the filtrate was concentrated in vacuo. The residue was mixed with isopropanol (300 mL) and reaction mixture was heated to 78°C (±2). The mixture was added to toluene (900 mL). The reaction mixture was gradually cooled to 28°C (±2) and stirred at this temperature for 3 hrs. The solid obtained was filtered, washed with toluene and dried under vacuo at 48°C (±2) to obtain (R)-2-[[2-(4-aminophenyl)ethyl]-amino]- I -phenylethanol monohydrochioride.Yield: 78.1 g (86.1percent); Purity by HPLC: 99.14 percent.Example-3: Preparation of (R)-2-[}2-(4-aminophenyl)ethyI]-amino]-l-phenyIethanoI monohydrochloride (or) (R)-2-(4-aminophenethylamino)-l-phenylethanol mono hydrocloride (FormuIa-6a) (R)-2-[[2'-(4-nitrophenyl)-ethyl]amino]- 1 -phenylethanol monohydrochloride compound of formula-5a (50 gms), methanol (500 ml) and 5percent Pd/C (5 gm) were charged into an autoclave vessel. 4-5 kg/cm hydrogen gas pressure was applied to the reaction mixture at 45-50°C and stirred for 6 hrs at the same temperature and pressure. Cooled the reaction mixture to 25-30°C and filtered through hyflo bed. Distilled off the solvent completely from the filtrate under reduced pressure and co-distilled with cyclohexane. 150 ml of cyclohexane was added to the obtained compound, heated the reaction mixture to reflux temperature and stirred for 45 min at the same temperature. Cooled the reaction mixture to 25-30°C and stirred for 45 mins at the same temperature. Filtered the precipitated solid, washed with cyclohexane and dried to get the title compound. Yield: 35.0 gms.Method-Ca’): 88.0 gm of (R)- 1 -Phenyl-2- [ [2-(4-nitrophenyl)ethyl] amino] ethanolhydrochloride of formula (2) obtained in step-I was dissolved in 1320 ml of methanol and transfened into hydrogenator vessel containing 8.8 gms of Raney-nickel. The resultantreaction suspension was agitated under 6 kg/cm2 to 8 kg/cm2 hydrogen gas pressure at about45°C for about 8 hours. The reaction progress was monitored by TLC (thin layer chromatography). After completion of reaction, reaction mass was cooled to about 30°C, the reaction suspension was filtered on celite bed to separate the catalyst and washed with methanol. The filtrates were combined and concentrated under reduced pressure to givecrude product as liquid. The resulting crude product was suspended in 260 ml of ethyl acetate and stined for about 1 hour at about 30°C. The solid separated was filtered and the solid obtained was washed with ethyl acetate followed by drying the solid to yield 72 gms of (R)- 1 -phenyl-2- [ [2-(4-aminphenyl)ethyl] amino] ethanol monohydrochloride of formula (10) as crystalline solid.SOR: []25 -38.7° (c=0.5 in MeOH);FTIR(KBr):3357, 3391, 2956, 1612, 1519, 1449, 1406, 1272, 1098, 1052, 924, 821, 756, 699 cm1 ‘H-NMR (400 MHz, DMSO-d6): ö (ppm) = 2.84-2.86 (m, 2H), 2.98-3.13 (m, 4H), 5.03 (d, 3H), 6.22 (s, 1H), 6.51 (d, J=7.5 Hz, 2H), 6.86 (d, J=7.5 Hz, 2H), 7.28-7.37 (m, 5H), 9.3 (br s, 2H).‘3C-NMR (400 MHz, DMSO-d6): ö (ppm)= 30.9, 48.9, 53.9, 68.5, 114.5, 124.4, 126.2, 128.0, 128.6, 129.3, 142.2, 147.5.MS: mlz=257 (M+H).
Computed Properties
Molecular Weight:256.34
XLogP3:1.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:256.157563266
Monoisotopic Mass:256.157563266
Topological Polar Surface Area:58.3
Heavy Atom Count:19
Complexity:233
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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