| 99% |
With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; 2-methoxy-2-methylpropane at 80℃; for 48h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube; |
|
| 99% |
Stage #1: N,N‐dimethylbenzamide With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; 2-methoxy-2-methylpropane at 20℃; for 48h; Sealed tube;
Stage #2: With hydrogenchloride In tetrahydrofuran; 2-methoxy-2-methylpropane; lithium hydroxide monohydrate at 20℃; for 6h; |
1.1.1 Example 1.1
In an argon glove box, add NaOH (0.4mg, 10.0μmol), MTBE (1.5mL) and BEt3 (10.0μL, 1mmol/mL in THF, 10.0μmol) into a 10mL sealed tube,Stir at room temperature for 2 minutes in the glove box;Then, add tertiary amide(N,N-dimethylbenzamide, 149.1mg, 1.0mmol) and PhSiH3 (123.4μL, 1.0mmol); tighten the tube and transfer it out of the glove box,Stir at room temperature for 48 hours;Subsequently, add 20mL of dilute hydrochloric acid (1mmol/mL), and stir at room temperature for 6h;Finish the reaction, extract three times (3×10 mL) with 1 mmol/mL dilute hydrochloric acid, combine the aqueous phases, add 4 mmol/mL sodium hydroxide aqueous solution (20 mL) to the combined aqueous phase, and stir at room temperature for 6 hours;After finishing the reaction, extract three times with ether (3×15mL), combine the organic phases, wash the combined organic phases with saturated brine, dry with anhydrous sodium sulfate, filter, and concentrate to obtain a colorless liquid, which is the desired tertiary amine ( 133.2mg, the yield was 99%). |
| 98% |
With Ν,Ν-dimethylethylamine alane In tetrahydrofuran; toluene at 25℃; for 0.5h; |
|
| 98% |
With bis(2-chlorophenyl)borinic acid; phenylsilane In neat (no solvent) at 20℃; for 12h; Sealed tube; Inert atmosphere; |
|
| 96% |
With triethylamine alane In tetrahydrofuran for 0.5h; Ambient temperature; |
|
| 96.3% |
Stage #1: N,N‐dimethylbenzamide With borane-2-methyltetrahydrofuran complex In 2-methyltetrahydrofuran at 20℃; for 12.0167h; Heating / reflux;
Stage #2: With methanol In 2-methyltetrahydrofuran at 0℃; |
22
Example 22: Reduction of N,N-dimethylbenzamide with borane complex of 2- methyltetrahydrofuran; 98 ml of a 1 M solution of BH3 - 2-MeTHF (0.098 mol) were added over 1 minute to 11.48 g (0.085 mol) of N,N-dimethylbenzamide in 100 ml 2-methyltetrahydrofuran at ambient temperature and stirred for 12 hours. After cooling to 0°C 8 ml of methanol were slowly added and then the mixture was extracted with 100 ml of saturated aqueous Na2CO3 solution. The organic layer was dried over sodium sulfate. Analysis of the organic layer gave a yield of 96.3 % of dimethylbenzylamine. |
| 96% |
Stage #1: N,N‐dimethylbenzamide With 1,1,3,3-Tetramethyldisiloxane; [((CH3)5C5)IrCl((CH3)2NC6H3C5H4N)]; triphenylmethylium tetrakis(pentafluorophenyl)borate In 1,1,2,2-tetrachloroethane at 100℃; for 0.5h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: With hydrogenchloride In diethyl ether; lithium hydroxide monohydrate for 0.166667h; Inert atmosphere; Schlenk technique; Glovebox; chemoselective reaction; |
|
| 95.1% |
Stage #1: N,N‐dimethylbenzamide With borane-THF In tetrahydrofuran at 20℃; for 12.0167h; Heating / reflux;
Stage #2: With methanol In 2-methyltetrahydrofuran at 0℃; |
23
Example 23 (comparative): Reduction of N,N-dimethylbenzamide with borane complex of tetrahydrofuran; 98 ml of a 1 M solution of BH3 - THF (0.098 mol) were added over 1 minute to 1 1.48 g (0.085 mol) of N,N-dimethylbenzamide in 100 ml tetrahydrofuran at ambient temperature and stirred for 12 hours. After cooling to 0°C 8 ml of methanol were slowly added and then the mixture was extracted with 100 ml of saturated aqueous Na2CO3 solution. The organic layer was dried over sodium sulfate. Analysis of the organic layer gave a yield of 95.1 % of dimethylbenzylamine. |
| 95% |
With dihydrogen hexachloroplatinate(IV) hexahydrate In tetrahydrofuran at 60℃; for 3h; |
|
| 95% |
With bis(η5-cyclopentadienyl)zirconium dihydride; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; |
1-13
The bis(cyclopentadiene) zirconium dihydride (denoted as Cp2ZrH2, 0.02mmol, 4.46mg), N,N-dimethylbenzamide (denoted as 1a, 0.2mmol, 29.8mg), pinacol borane (Denoted as HBpin, 0.6mmol, 87μL) and tetrahydrofuran (1 mL) were mixed, and stirred at room temperature under nitrogen (1atm) atmosphere for 12h to obtain a product system containing the structure compound represented by formula 2a. The yield of NMR analysis was 95%. |
| 95% |
Stage #1: N,N‐dimethylbenzamide With bis(η5-cyclopentadienyl)zirconium dihydride; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 12h; Glovebox; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether; lithium hydroxide monohydrate for 2h; Glovebox; Inert atmosphere; |
2. Experimental
In a nitrogen-filled glovebox, to a 15 mL reaction tube equipped with a magnetic stirrer, were added Cp2ZrH2 (0.01mmol, 2.2 mg) as the catalyst, and the appropriate amide (0.2mmol); solvent was added when necessary. HBpin (3 equiv. peramide functional group) was then added, and the reaction tube was taken out from the glovebox and stirred at room temperature for 12-48 h. The resultant crude amines were either isolated using silica gel flash chromatography, or acidified by stirring with HCl in Et2O (2 mL, 1N) for 2 h, after which time precipitation was observed. Then, the reaction solution was transferred to a centrifuge tube and centrifuged three times. The supernatant was removed and the resulting solid was dried inan oven at 80 °C for several hours to obtain the HCl salt of the amine. |
| 95% |
With phenylsilane-d3; C36H48F6N6NiO5S2 In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique; |
|
| 95% |
Stage #1: N,N‐dimethylbenzamide With oxalyl dichloride; hydrogen; tris(2,6-difluorophenyl)borane In chloroform at 60℃; for 22h; Glovebox; Sealed tube;
Stage #2: With anhydrous sodium carbonate In lithium hydroxide monohydrate |
3.1.8 General procedure for FLP-catalyzed hydrogenation of tertiary amides
General procedure: In a glovebox B(2,6-F2-C6H3)3 (3c) (3.7 mg, 10.6 μmol, 2.0 mol%, or 9.3 mg, 26.5 μmol, 5.0 mol%) and N,N-disubstituted carboxamide substrate 1 (530 μmol, 1.00 equiv.) were placed in a crimp seal glass vial and dissolved in 3.2 mL abs. CHCl3. Oxalyl chloride (101 mg, 795 μmol, 1.50 equiv.) was subsequently added to the vial. The sample was then transferred to a stainless steel high pressure reactor and charged with hydrogen (80 bar). The reactor was heated with an oil bath at 40 °C to 70 °C for 22 h to 48 h. Subsequently, the reactor was cooled to room temperature and depressurized[SI12]. Purification method for isolation as ammonia salt: The product mixture was filtered through glass wool and the solvent was evaporated under reduced pressure. The crude product was then suspended in Et2O using an ultrasonic bath. The suspension was subsequently centrifuged (3000 rpm for 10 min) and the supernatant solvent was pipetted off. This washing cycle was repeated two times. Finally, the white to lightly colored ammonia salt was dried under reduced pressure and analyzed by NMR spectroscopy and mass spectrometry[SI12]. Purification method for isolation as amine: The product mixture was washed once with sat. aq. Na2CO3. The phases were separated, and the aqueous phase was extracted three times with CHCl3 (when phase separation did not occur, Et2O was added as organic solvent). The combined organic phases were loaded with a small portion of silica and evaporated to dryness. The dry powder was subjected to column chromatography. The colorless to lightly colored amine was subsequently analyzed by NMR spectroscopy and mass spectrometry[SI12]. |
| 92% |
With Dimethylphenylsilane In toluene at 110℃; for 3h; Inert atmosphere; |
|
| 91% |
With phenylsilane; C20H25Cl2CoN3; sodium triethylborohydride In 1,2-dimethoxyethane at 30℃; for 6h; Inert atmosphere; |
33 Example 33: Reduction of N,N-dimethylbenzamide to N,N-dimethylbenzylamine:
Under an inert atmosphere, the substrate N,N-dimethylbenzamide (149 mg, 1 mmol), phenylsilane (216 mg, 2 mmol), Co-2 catalyst (9.0 mg, 0.02 mmol),sodium triethylborohydride (40 μL, 0.04 mmol) were sequentially added to the reaction tube. and ethylene glycol dimethyl ether (2 mL), and the resulting mixture was stirred well.The reaction was carried out in an oil bath at 30°C for 6 hours. The reaction system was cooled to room temperature, diluted and quenched with ethyl acetate, and concentrated. The crude product was subjected to flash silica gel column chromatography to obtain 123 mg of light yellow oily liquid, yield: 91%. |
| 90% |
With diethoxymethylane; Zinc acetate In tetrahydrofuran at 65℃; Inert atmosphere; chemoselective reaction; |
|
| 90% |
With phenylsilane; potassium hydroxide In neat (no solvent) at 20℃; for 3h; |
|
| 90% |
With C25H42N6Rh(1+)*F6Sb(1-); phenylsilane In neat (no solvent) at 30℃; for 20h; Glovebox; Inert atmosphere; Sealed tube; |
|
| 90% |
With triphenylborane; dihydromethylphenylsilane In dichloromethane-d2 at 25℃; for 6h; Inert atmosphere; chemoselective reaction; |
|
| 90% |
With borane-ammonia complex; boron trifluoride diethyl ether complex; tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃; for 24h; |
|
| 90% |
With 1,1,3,3-Tetramethyldisiloxane In ethyl acetate at 20 - 80℃; for 16h; Green chemistry; |
|
| 90% |
Stage #1: N,N‐dimethylbenzamide With 0.55C27H43N3Si3V*0.45C27H44N3Si3V; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 60℃; for 16h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;
Stage #2: In tetrahydrofuran chemoselective reaction; |
|
| 89% |
With [Fe3(H)(CO)11]2{Fe(DMF)4}; 1,2-bis(dimethylsilyl)benzene In toluene at 100℃; for 0.5h; Inert atmosphere; |
|
| 88% |
With sodium tetrahydridoborate; zirconium tetrachloride In tetrahydrofuran for 5h; Ambient temperature; |
|
| 88% |
With dihydrogen hexachloroplatinate(IV) hexahydrate; 1,1,3,3-Tetramethyldisiloxane In tetrahydrofuran; toluene at 75℃; for 5h; Inert atmosphere; |
|
| 88% |
With (5-bromobenzo[b]thiophen-2-yl)boronic acid; phenylsilane In toluene at 110℃; for 40h; Inert atmosphere; Schlenk technique; chemoselective reaction; |
|
| 87% |
With phenylsilane; Cs2CO3 at 20℃; for 24h; Schlenk technique; |
|
| 85% |
With n-butyllithium; 1-(2-hydroxy-2-phenylethyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate; ferrous acetate; lithium chloride In tetrahydrofuran at 65℃; for 7h; Inert atmosphere; |
|
| 84% |
With sodium tetrahydridoborate; <i>N</i>,<i>N</i>-dimethyl-aniline; anhydrous zinc chloride In tetrahydrofuran for 2h; Heating; |
|
| 84% |
Stage #1: N,N‐dimethylbenzamide With triruthenium dodecacarbonyl; 1,1,3,3-tetramethyldisiloxane In toluene at 20 - 50℃; for 24.17h; Inert atmosphere;
Stage #2: With hydrogenchloride In 1,4-dioxane; ethyl acetate; toluene at 20℃; for 0.5h;
Stage #3: With sodium hydroxide In dichloromethane; lithium hydroxide monohydrate at 20℃; for 0.5h; |
|
| 82% |
With hydrogenchloride; dimethylsulfide borane complex; boron trifluoride diethyl ether complex In tetrahydrofuran for 0.25h; Heating; other tertiary and secondonary amides; |
|
| 80% |
With [(1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimid-2-ylidene)CuOtBu] In tetrahydrofuran at 50℃; for 24h; Inert atmosphere; |
|
| 78% |
With tert-butyl-N-methyl-N-isopropylamine-borane In 1,4-dioxane for 0.25h; Heating; |
|
| 77% |
With tetrahydropyran; PMHS; (μ3,η2:η3:η5-acenaphthalene)Ru3(CO)7 at 40℃; for 15h; |
|
| 76% |
With DEANB/5 mol% SpiroCAT formulation In tetrahydrofuran at 50℃; for 3.5h; |
|
| 75% |
With borane-N-ethyl-N-isopropylaniline complex In 1,4-dioxane for 0.25h; Heating; |
|
| 75% |
With PMHS In tetrahydrofuran at 60℃; for 3h; |
|
| 75% |
With H2SiEt2 In benzene at 70℃; |
|
| 69% |
Stage #1: N,N‐dimethylbenzamide With triethyloxonium tetra-fluoroborate In dichloromethane at 20℃;
Stage #2: With platinum on carbon; hydrogen; sodium methoxide In ethanol at 25℃; Cooling with ice; |
10
General procedure: A solution of carboxylic acid amide (20 mmol) in dichloromethane (10 ml) is admixed with triethyloxonium tetrafluoroborate (4.18 g, 22 mmol) and stirred either (A) overnight at room temperature or (B) for 3 hours on the water bath at 40° C. under argon. Then, the mixture is concentrated in vacuo and the residue is taken up in 20 ml of absolute ethanol. An autoclave cooled in the ice bath is charged with catalyst (1 mol %) and 10 ml of 2M sodiummethylate solution in ethanol, flushed with argon and filled with the reaction solution in ethanol. 40 bar of hydrogen are then injected in, and the mixture is stirred at 25° C. and a constant pressure until hydrogen absorption is no longer evident (1-12 h). After filtration over Celite, the filtrate is dissolved in 11 ml of 2N hydrochloric acid and washed with diethyl ether, the aqueous phase is rendered basic with 14 ml of 2N NaOH solution, the amine is extracted with diethyl ether, and the combined organic phases are dried over K2CO3. After drawing off the solvent in vacuo, virtually clean amine is obtained. (0186) The catalysts used and yields can be found in Table 6. |
| 68% |
Stage #1: N,N‐dimethylbenzamide With triethyloxonium tetra-fluoroborate In dichloromethane for 16h;
Stage #2: With platinum on carbon; hydrogen; potassium etoxide In ethanol at 25℃; for 16h; |
|
| 64% |
Stage #1: N,N‐dimethylbenzamide With dicobalt octacarbonyl In toluene at 100℃; for 3h; Schlenk technique; Inert atmosphere;
Stage #2: With sodium hydroxide In methanol; lithium hydroxide monohydrate; toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere; chemoselective reaction; |
|
| 59% |
With sodium tetrahydridoborate; methanesulfonic acid In dimethyl sulfoxide at 70℃; for 2h; |
|
| 57% |
With phenylsilane; C36H61FeN2PSi2 In benzene at 80℃; for 1h; Inert atmosphere; Sealed tube; |
|
| 52% |
Stage #1: N,N‐dimethylbenzamide With triethyl borane; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane; potassium hydroxide In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
Stage #2: With lithium hydroxide monohydrate; sodium hydroxide In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube; |
|
| 40% |
With lithium tetrahydridoborate In diethyl ether at 25℃; for 24h; rate of reduction; |
|
|
With borane-N-ethyl-N-isopropylaniline complex In tetrahydrofuran Ambient temperature; |
|
|
With diisobutylaluminium hydride |
|
|
With sulfuric acid durch elektrolytische Reduktion; |
|
|
With hydrogenchloride; dimethylsulfide borane complex 1.) THF, reflux, 15 min, 2.) 100 deg C, 30 min; Yield given. Multistep reaction; |
|
|
With N,N,N,N,-tetramethylethylenediamine; dimethylsulfide borane complex; boron trifluoride diethyl ether complex 1.) THF, 0.25 h, 2.) ether, 30 min; Yield given. Multistep reaction; |
|
| 64 % Chromat. |
With sodium tetrahydridoborate; Diethylselenium diiodide In tetrahydrofuran for 20h; Heating; |
|
|
With hydrogenchloride; borane N,N-diethylaniline complex 1.) THF, 8 h, reflux; Yield given. Multistep reaction; |
|
| 99.5 % Chromat. |
With triethylsilane; diethylamine In toluene at 100℃; |
|
| 65 % Chromat. |
With sodium tetrahydridoborate; lithium chloride In diethylene glycol dimethyl ether at 162℃; for 2h; |
|
|
Multi-step reaction with 2 steps
1: 89 percent / dimer of p-methoxyphenylthionophosphine sulfide / toluene / 5 h / 85 - 110 °C
2: 1.) triethyloxonium tetrafluoroborate, 2.) NaBH4 / 1.) CH2Cl2, 25 deg C, 10-20 min; 2.) anhydrous methanol, 1-2 h |
|
|
With Dimethylphenylsilane In hexadeuterobenzene at -78 - 20℃; |
|
| 93 %Chromat. |
With dodecacarbonyltri-iron In toluene at 100℃; for 24h; Inert atmosphere; |
|
| 97 %Chromat. |
With Triethoxysilane; Zinc acetate In tetrahydrofuran at 20℃; Inert atmosphere; |
|
|
With H2SiEt2; [(POCOP)Ir(H)(acetone)]+[B(C6F5)4]- In chlorobenzene-d5 at 60℃; for 1h; Inert atmosphere; |
|
| 81 %Chromat. |
With benzo[b]thiophen-5-yl-amine; benzo[b]thiophene-2-boronic acid; phenylsilane In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; |
|
| > 95 %Spectr. |
Stage #1: N,N‐dimethylbenzamide With phenylsilane; lithium triethylhydroborate In tetrahydrofuran at 60℃; for 2h; Inert atmosphere; Schlenk technique;
Stage #2: With lithium hydroxide monohydrate In methanol at 20℃; for 2h; |
|
| > 99 %Chromat. |
With tris(pentafluorophenyl)borate In toluene at 100℃; for 18h; Sealed tube; Inert atmosphere; |
|
| 99 %Chromat. |
With Pt(I<SUP>t</SUP>Bu)(divinyltetramethyldisiloxane); diphenylsilane In tetrahydrofuran at 40℃; for 1h; Schlenk technique; Inert atmosphere; |
|
| 86.3 %Spectr. |
With [{κ3-N,Si,C-PhB(4,4-dimethyl-2-oxazoline)((4,4-dimethyl-2-oxazoline)SiHPh)(1-mesitylimidazole)}Rh(H)CO][HB(C6F5)3]; phenylsilane In chloroform-d1 at 80℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox; |
|
|
With [(SIMes)PFMe2][B(C6F5)4]2; phenylsilane at 100℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox; |
|
| 100 %Chromat. |
With dodecacarbonyltri-iron; (2-methyl-2-((phenylthio)methyl)propane-1,3-diyl)bis(phenylsulfane); diphenylsilane In toluene at 100℃; for 16h; Inert atmosphere; Schlenk technique; |
|
| > 90 %Chromat. |
With phenylsilane; [(k2-P,N)Mn(N(SiMe3)2)] In hexadeuterobenzene at 75℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; |
|
| > 99 %Spectr. |
With phenylsilane; cobalt bis(acetylacetonate); bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran-d8 at 60℃; for 24h; Inert atmosphere; Sealed tube; |
|
|
With dimethylbis(η5-pentamethylcyclopentadienyl)thorium; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexadeuterobenzene at 70℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; |
|
| 88 %Spectr. |
With manganese(II) bis[bis(trimethylsilyl)amide]; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexadeuterobenzene at 50℃; for 20h; Inert atmosphere; Glovebox; |
|
|
With Triethoxysilane; potassium-t-butoxide In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; chemoselective reaction; |
|
| 92 %Spectr. |
With 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexadeuterobenzene at 60℃; for 16h; Glovebox; Schlenk technique; Inert atmosphere; |
|
|
With La(CH<SUB>2</SUB>C<SUB>6</SUB>H<SUB>4</SUB>NMe<SUB>2</SUB>-o)<SUB>3</SUB>; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexadeuterobenzene at 25℃; for 4h; Glovebox; Inert atmosphere; |
|
|
Stage #1: N,N‐dimethylbenzamide With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.5h; Autoclave;
Stage #2: With lithium dimethylaminoborohydride In tetrahydrofuran at 120℃; for 5h; |
1 (Example 1) Production of Amine Using Lithium Dimethylamino Borohydride
Each amide in an amount of 200 mg and a THF solution of tert-butylmagnesium chloride (1.0 M, 1.25 eq.) were added to a 50 mL autoclave, followed by stirring at room temperature for 30 minutes. Thereafter, a THF solution of lithium dimethylamino borohydride (1.0 M, 1.25 eq.) was added thereto, followed by stirring at a bath temperature of 120° C. for 5 hours. The reaction mixture was cooled to room temperature, and then quenched with methanol, and the product was confirmed by GC. The results are shown in Table 1 below. |
| 87 %Spectr. |
With 1,3-diphenyldisiloxane; Zinc acetate In lithium hydroxide monohydrate; ethyl acetate at 23℃; for 24.5h; Inert atmosphere; |
Reduction of Tertiary Amides; General Procedure
General procedure: To a tared 2-dram vial were added EtOAc (0.500 mL, 0.500 M), DPDS(115 mg, 0.500 mmol, 2.00 equiv), and zinc acetate (4.60 mg, 0.025mmol, 10.0 mol%). The vial was capped and the contents stirred at550 rpm for 30 minutes. After this time, the corresponding tertiaryamide (0.250 mmol, 1.00 equiv) was added and the resulting mixturewas stirred at 23 °C for 24 hours. The reaction mixture was blown dry(nitrogen gas), and Qnmr was performed using hexamethylbenzeneas an internal standard. For isolation, the reaction mixture was dilutedwith EtOAc (3.5 mL) and 2 M NaOH (3 mL). This mixture was left tostir for 1 hour before extraction with EtOAc (3 × 4 mL). The combinedorganics were dried over MgSO4 and concentrated under reducedpressure. Purification by flash chromatography afforded the targetamine. Purification by flash chromatography was performed to confirm conversion,but resulted in loss of product, hence, calculated yields (determinedby 1H NMR analysis using hexamethylbenzene as an internalstandard) and not isolated yields are reported below. In certaincases, siloxane impurities co-eluted with the amine of interest as a resultof their polar nature and are observed as impurities in the aromaticregion of the NMR spectra. N,N-Dimethyl-1-phenylmethanamine (1)The title compound was prepared following the general procedure.Purification by flash chromatography on basic alumina (3:1 hexanes/EtOAc to EtOAc) afforded amine 1.Yield: 87%; colorless oil.IR: 3028, 2976, 2943, 2857, 2816, 2766, 1454, 1364 cm-1.1H NMR (400 MHz, CDCl3): = 7.35-7.28 (m, 1 H), 7.29 (s, 3 H), 7.30-7.19 (m, 1 H), 3.41 (s, 2 H), 2.23 (s, 6 H); the spectra matched thosepreviously reported.12HRMS (CI): m/z [M + H]+ calcd for C9H14N: 136.1126; found: 136.1135(error 6.6 ppm). |
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