(R)-3-iodo-1-phenyl-1-propanol
methylamine
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 23℃; for 2h; | 99% |
In tetrahydrofuran; water at 25℃; for 12h; Inert atmosphere; enantioselective reaction; | 98% |
In tetrahydrofuran; water at 20℃; | 85% |
(R)-(3-hydroxy-3-phenylpropyl)carbamic acid ethyl ester
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Heating; | 93% |
With lithium aluminium tetrahydride In tetrahydrofuran Heating; | 89% |
β-Methylaminoethyl phenyl ketone hydrochloride
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
With Rh[((R,R)-BenzP*)(cod)]SbF6; hydrogen; caesium carbonate; zinc(II) chloride In methanol at 20℃; under 19001.3 Torr; for 48h; Autoclave; enantioselective reaction; | 93% |
Multi-step reaction with 2 steps 1: potassium borohydride / tetrahydrofuran / 66 °C 2: sodium hydrogencarbonate / chloroform; water View Scheme |
(1R) 3-phenyl-3-hydroxypropyl methanesulfonate
methylamine
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 65℃; for 24h; | 91% |
In tetrahydrofuran; water at 60 - 65℃; for 4h; | 80% |
In tetrahydrofuran; water at 65℃; for 3h; | 837 mg |
N-methyl-3-phenylprop-2-en-1-amine
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Stage #1: N-methyl-3-phenylprop-2-en-1-amine With L-diisopinocampheylborane In 1,2-dimethoxyethane at 30℃; for 2h; Stage #2: With dihydrogen peroxide; potassium hydroxide In 1,2-dimethoxyethane at 20℃; for 2h; | 90.67% |
(R)-6-phenyl-1,3-oxazinan-2-one R-7a
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran Heating; | 90% |
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Reflux; | 86% |
Phenyl vinyl ketone
methylamine
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Stage #1: Phenyl vinyl ketone; methylamine With sodium carbonate In water; isopropyl alcohol at 20℃; for 2h; Inert atmosphere; Stage #2: With chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); sodium formate In water; isopropyl alcohol at 40℃; for 10h; pH=7; Inert atmosphere; enantioselective reaction; | 79% |
(1R)-3-chloro-1-phenylpropanol
methylamine
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
With potassium iodide In methanol; water at 80℃; for 8h; | 72% |
With sodium iodide In water |
3-methylamino-1-phenyl-propan-1-ol; hydrochloride
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Stage #1: 3-methylamino-1-phenyl-propan-1-ol; hydrochloride With sodium hydrogencarbonate In chloroform; water Stage #2: With (S)-Mandelic acid In acetone | 46% |
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran Heating; |
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol for 20h; Ambient temperature; Yield given; |
methylamine
3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate
A
(S)-N-methyl-3-amino-1-phenyl-1-propanol
B
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate With 3 A molecular sieve; oxygen; (-)-sparteine; palladium diacetate In toluene at 80℃; under 760 Torr; for 36h; Stage #2: methylamine With water In tetrahydrofuran at 65℃; |
(6R)-2-((S)-1-triisopropylsilyloxyethyl)-3-methyl-6-phenyl-1,3-oxazinane
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 90℃; for 1.5h; |
Benzoylacetonitrile
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 74 percent / borane-dimethylsulfide complex; polymer-supported chiral sulfonamide / tetrahydrofuran / Heating 2: sodium hydrogen carbonate / CH2Cl2; H2O / 2 h / 20 °C 3: 93 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating View Scheme |
(1R)-3-amino-1-phenyl-1-propanol
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydrogen carbonate / CH2Cl2; H2O / 2 h / 20 °C 2: 93 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 88 percent / K2CO3 / CH2Cl2; H2O / 20 °C 2: 89 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme | |
Multi-step reaction with 2 steps 1: NaHCO3 / tetrahydrofuran 2: LiAlH4 / tetrahydrofuran / Heating View Scheme |
butyric acid 2-ethoxycarbonyl-1-phenyl-ethyl ester
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C 2: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 3: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 4: 80 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme |
Ethyl 3-hydroxy-3-phenylpropanoate
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: DCC; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C 2: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C 3: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 4: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 5: 80 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: 85 percent / lithium aluminum hydride / tetrahydrofuran / 2 h 2.1: 95 percent / Et3N / CH2Cl2 / 0 h / -10 °C 3.1: O2; (-)-sparteine; 3 Angstroem sieves / Pd(OAc)2 / toluene / 36 h / 80 °C / 760 Torr 3.2: H2O / tetrahydrofuran / 65 °C View Scheme |
ethyl (R)-3-hydroxy-3-phenylpropanoate
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 2: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 3: 80 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme | |
Multi-step reaction with 3 steps 1: 86 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 1.5 h / 0 - 20 °C 2: 82 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C 3: 91 percent / tetrahydrofuran; H2O / 24 h / 65 °C View Scheme |
(R)-3-phenyl-1,3-dihydroxypropane
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 2: 80 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme | |
Multi-step reaction with 2 steps 1: 82 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C 2: 91 percent / tetrahydrofuran; H2O / 24 h / 65 °C View Scheme | |
Multi-step reaction with 2 steps 1: 74 percent / triethylamine / diethyl ether / 3 h / -10 - 0 °C 2: 837 mg / H2O; tetrahydrofuran / 3 h / 65 °C View Scheme |
benzaldehyde
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: tetrahydrofuran; hexane / 1 h / -78 °C 2.1: DCC; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C 3.1: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C 4.1: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 5.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 6.1: 80 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme |
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / 20 °C 2: diphenyl silane / tris(triphenylphosphine)rhodium(I) carbonyl hydride / tetrahydrofuran / 15 h / 20 °C 3: HCl / methanol; H2O / 1.5 h / 90 °C View Scheme |
(6R)-2-((S)-1-triisopropylsilyloxyethyl)-3-methyl-6-phenyl-1,3-oxazinan-4-one
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diphenyl silane / tris(triphenylphosphine)rhodium(I) carbonyl hydride / tetrahydrofuran / 15 h / 20 °C 2: HCl / methanol; H2O / 1.5 h / 90 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 80 percent / ethanol; H2O / 20 °C 2: 46 percent / Pseudomonas cepacia lipase on modified ceramic particles / diisopropyl ether / 16 h / 27 °C 3: 88 percent / BH3*SMe2 / tetrahydrofuran / Heating 4: 88 percent / K2CO3 / CH2Cl2; H2O / 20 °C 5: 89 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme |
3-hydroxy-3-phenylpropanenitrile
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 46 percent / Pseudomonas cepacia lipase on modified ceramic particles / diisopropyl ether / 16 h / 27 °C 2: 88 percent / BH3*SMe2 / tetrahydrofuran / Heating 3: 88 percent / K2CO3 / CH2Cl2; H2O / 20 °C 4: 89 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme | |
Multi-step reaction with 3 steps 1: hydrogen, NH3 / Raney Ni / ethanol / 90 °C / p(NH3) = 30 psi and p(H2) = 170 psi 2: NaHCO3 / tetrahydrofuran 3: LiAlH4 / tetrahydrofuran / Heating View Scheme |
(R)-3-acetyloxy-3-phenylpropanenitrile
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 88 percent / BH3*SMe2 / tetrahydrofuran / Heating 2: 88 percent / K2CO3 / CH2Cl2; H2O / 20 °C 3: 89 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme |
ethyl 3-oxo-3-phenylpropionate
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / H2 / RuBr2((S)-(6,6'-(MeO)2-biphenyl-2,2'-diyl)bis(Ph2-phosphane) / ethanol / 18 h / 50 °C / 760.05 Torr 2: 86 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 1.5 h / 0 - 20 °C 3: 82 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C 4: 91 percent / tetrahydrofuran; H2O / 24 h / 65 °C View Scheme |
1-phenyl-1,3-propanediol
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 95 percent / Et3N / CH2Cl2 / 0 h / -10 °C 2.1: O2; (-)-sparteine; 3 Angstroem sieves / Pd(OAc)2 / toluene / 36 h / 80 °C / 760 Torr 2.2: H2O / tetrahydrofuran / 65 °C View Scheme |
3-(benzyl methylamino)-1-phenylpropan-1-one hydrochloride
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2, 2, (2S,4S)-N-(methylcarbamoyl)-4-(dicyclohexylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine / methanol / 48 h / 50 °C / 22800 Torr 2: H2 / 5percent Pd/C / ethanol / 20 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 50 percent / concd. HCl / ethanol / 4 h / Heating 2: H2, 2, (2S,4S)-N-(methylcarbamoyl)-4-(dicyclohexylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine / methanol / 48 h / 50 °C / 22800 Torr 3: H2 / 5percent Pd/C / ethanol / 20 h / Ambient temperature View Scheme |
ortho-methylphenyl iodide
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
atomoxetine hydrochloride
Conditions | Yield |
---|---|
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium carbonate; copper(l) iodide In toluene at 148℃; for 21h; Ullmann type reaction; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With sodium hydroxide In water pH=11 - 12; | 99% |
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium carbonate; copper(l) iodide In toluene at 148℃; for 21h; Ullmann type reaction; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With sodium hydroxide In water pH=11 - 12; | 94% |
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium phosphate; copper(l) iodide In toluene for 24h; Ullmann type reaction; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With sodium hydroxide In water pH=12 - 14; | 82% |
4-chlorobenzotrifluoride
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
(R)-fluoxetine
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide at 80 - 90℃; for 1h; | 92% |
In N,N-dimethyl acetamide | 86% |
In N,N-dimethyl acetamide | 86% |
2-Fluorotoluene
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
(R)-tomoxetine
Conditions | Yield |
---|---|
Stage #1: (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium hydroxide In dimethyl sulfoxide at 130℃; for 1h; Stage #2: 2-Fluorotoluene In dimethyl sulfoxide at 130℃; | 89.51% |
Stage #1: (R)-N-methyl-3-phenyl-3-hydroxypropylamine With sodium hydride In dimethyl sulfoxide for 0.25h; Stage #2: With Potassium benzoate In dimethyl sulfoxide at 50 - 55℃; for 1h; Stage #3: 2-Fluorotoluene In dimethyl sulfoxide at 50 - 120℃; for 6.25 - 7.25h; | |
With potassium tert-butylate In dimethyl sulfoxide at 60℃; for 8h; |
4-Fluorobenzotrifluoride
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
(R)-fluoxetine
Conditions | Yield |
---|---|
Stage #1: (R)-N-methyl-3-phenyl-3-hydroxypropylamine With sodium hydride In N,N-dimethyl acetamide; paraffin oil at 90℃; for 0.5h; Inert atmosphere; Stage #2: 4-Fluorobenzotrifluoride In N,N-dimethyl acetamide; paraffin oil at 100℃; for 5h; Inert atmosphere; | 88% |
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
atomoxetine hydrochloride
Conditions | Yield |
---|---|
Stage #1: (R)-N-methyl-3-phenyl-3-hydroxypropylamine; C7H7X In ethyl acetate at 77℃; Stage #2: With hydrogenchloride In water; acetone pH=1 - 2; | 73% |
2-Fluorotoluene
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
Conditions | Yield |
---|---|
With sodium hydride 1) DMSO, 2) DMSO; Yield given. Multistep reaction; |
2-methylchlorobenzene
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
(R)-tomoxetine
Conditions | Yield |
---|---|
With 2,4-dichlorophenoxyacetic acid dimethylamine; sodium hydride Multistep reaction; |
2-Chloroanisole
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
(R)-3-(2-methoxyphenoxy)-N-methyl-3-phenylpropan-1-amine
Conditions | Yield |
---|---|
With 2,4-dichlorophenoxyacetic acid dimethylamine; sodium hydride Multistep reaction; |
ortho-cresol
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
atomoxetine hydrochloride
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate Yield given. Multistep reaction; |
4-chlorobenzotrifluoride
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
(R)-fluoxetine hydrochloride
Conditions | Yield |
---|---|
With sodium hydride 1) DMSO, 50 deg C, 20 min, 2) DMSO, 90 deg C, 40 min; Yield given. Multistep reaction; | |
With sodium hydride 1.) N,N-dimethylacetamide, a) 0 deg C, 5 min, b) 70 deg C, 30 min, 2.) N,N-dimethylacetamide, 100 deg C, 3 h; Yield given. Multistep reaction; | |
With sodium hydride 1,) 0 deg C, then 70 deg C, 30 min; 2.) 2.5 h, 100 deg C; Yield given. Multistep reaction; |
The (R)-(+)-N-methyl-3-phenyl-3-hydroxypropylamine is an organic compound with the formula C10H15NO. The systematic name of this chemical is (1S)-3-(methylamino)-1-phenylpropan-1-ol. With the CAS registry number 115290-81-8, it is also named as benzenemethanol, α-[2-(methylamino)ethyl]-, (alphaS)-.
Physical properties about (R)-(+)-N-methyl-3-phenyl-3-hydroxypropylamine are: (1)ACD/LogP: 0.34; (2)#H bond acceptors: 2; (3)#H bond donors: 2; (4)#Freely Rotating Bonds: 5; (5)Polar Surface Area: 12.47 Å2; (6)Index of Refraction: 1.53; (7)Molar Refractivity: 50.2 cm3; (8)Molar Volume: 162.3 cm3; (9)Polarizability: 19.9×10-24cm3; (10)Surface Tension: 39.4 dyne/cm; (11)Density: 1.017 g/cm3; (12)Flash Point: 114.8 °C; (13)Enthalpy of Vaporization: 55.47 kJ/mol; (14)Boiling Point: 286.1 °C at 760 mmHg; (15)Vapour Pressure: 0.00126 mmHg at 25°C.
Uses of (R)-(+)-N-methyl-3-phenyl-3-hydroxypropylamine: it can be used to produce N-methyl-3,3-diphenylpropylamine. It will need reagent CF3SO3H. The yield is about 83%.
You can still convert the following datas into molecular structure:
(1)SMILES: O[C@H](c1ccccc1)CCNC
(2)InChI: InChI=1/C10H15NO/c1-11-8-7-10(12)9-5-3-2-4-6-9/h2-6,10-12H,7-8H2,1H3/t10-/m0/s1
(3)InChIKey: XXSDCGNHLFVSET-JTQLQIEIBS
(4)Std. InChI: InChI=1S/C10H15NO/c1-11-8-7-10(12)9-5-3-2-4-6-9/h2-6,10-12H,7-8H2,1H3/t10-/m0/s1
(5)Std. InChIKey: XXSDCGNHLFVSET-JTQLQIEISA-N
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