2-phenylpropan-2-amine (cumylamine) [CAS 585-32-0; InChIKey KDFDOINBXBEOLZ-UHFFFAOYSA-N; Reaxys, All

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30 reactions in Reaxys

2016-02-17 07h:13m:10s (EST)

NH 2

1. Query

Search as: As drawn

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N

N

N H 2N

Rx-ID: 1032543 View in Reaxys 1/30 Yield

Conditions & References

95 %

With lithium aluminium tetrahydride in diethyl ether, Time= 18h, T= 0 - 20 °C Metallinos, Costa; Nerdinger, Sven; Snieckus, Victor; Organic Letters; vol. 1; nb. 8; (1999); p. 1183 - 1186 View in Reaxys

94 %

With hydrogen in ethanol, Time= 12h Schneider, Cedric; Broda, Ellen; Snieckus, Victor; Organic Letters; vol. 13; nb. 14; (2011); p. 3588 - 3591 View in Reaxys

68 %

With lithium aluminium tetrahydride in diethyl ether, 1.) 12 h, 2.) reflux, 1 h Timberlake, Jack W.; Alender, Jeff; Garner, Archie W.; Hodges, Melvin L.; Oezmeral, Cenan; et al.; Journal of Organic Chemistry; vol. 46; nb. 10; (1981); p. 2082 - 2089 View in Reaxys

61.5 %

With lithium aluminium tetrahydride in diethyl ether, Time= 4h, Heating Leffler, J. E.; Zupancic, J. J.; Journal of the American Chemical Society; vol. 102; nb. 1; (1980); p. 259 - 267 View in Reaxys With lithium aluminium tetrahydride in diethyl ether, Heating Abramovitch,R.A.; Kyba,E.P.; Journal of the American Chemical Society; vol. 96; (1974); p. 480 - 488 View in Reaxys With nickel in isopropyl alcohol Balderman,D.; Kalir,A.; Synthesis; (1978); p. 24 - 26 View in Reaxys With lithium aluminium tetrahydride in diethyl ether, Time= 3h, Ambient temperature, Yield given Aelterman, Wim; Tehrani, Kourosch Abbaspour; Coppens, Wim; Huybrechts, Tom; De Kimpe, Norbert; Tourwe, Dirk; Declercq, Jean-Paul; European Journal of Organic Chemistry; nb. 1; (1999); p. 239 - 250 View in Reaxys With sodium chloride, nickel in ethanol, Electrolysis, Reduction Chan-Shing, Elisa Soazara; Boucher, Denys; Lessard, Jean; Canadian Journal of Chemistry; vol. 77; nb. 5-6; (1999); p. 687 - 694 View in Reaxys

19.8 g

With hydrogen, Lindlar's catalyst in ethanol, Time= 12h Blanchet, Jerome; Macklin, Todd; Ang, Patrick; Metallinos, Costa; Snieckus, Victor; Journal of Organic Chemistry; vol. 72; nb. 9; (2007); p. 3199 - 3206 View in Reaxys With hydrogen, Lindlar's catalyst in ethanol Ikeda, Hiroshi; Hoshi, Yosuke; Namai, Hayato; Tanaka, Futoshi; Goodman, Joshua L.; Mizuno, Kazuhiko; Chemistry - A European Journal; vol. 13; nb. 33; (2007); p. 9207 - 9215 View in Reaxys

O

NH H 2N

Rx-ID: 39261753 View in Reaxys 2/30

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Yield

Conditions & References

88 %

2.3 : EXAMPLE 2 Deacylation using ethylene diamine EXAMPLE 2 Deacylation using ethylene diamine (No.1) [0040] As shown by the reaction equation below, deacylation reaction was carried out with different types of amides as listed in Table 6-1 and Table 6-2. To 1.0 mmol of each amide and 1.0 equiv. of ammonium bromide was added 266 µL (4.0 equiv.) of ethylenediamine, followed by the reaction under microwave irradiation. The respective reaction conditions and product identification data (1H NMR data and 13C NMR data) are set out later together with the reaction equations. [Table 6-1] Entry No. Amide Reaction Temperature(°C) Reaction Time(hr.) Yield (percent)a 1 80 5 90 80 10 79b,c 90 10 90b,c 2 80 10 93 3 100 10 88 4 80 5 89 5 80 5 81(89°) 6 80 5 98 7 70 5 >99 8 70 5 >99 9 70 5 81(>99°) 10 70 5 97 11 70 5 >99 12 70 5 >99 12 70 5 96 13 70 5 99 14 70 5 99 a: Isolation Yield b: Ammonium bromide was 10molpercent. c: The yield was determined by 1H NMR analysis of the reaction mixture. [Table 6-2] Entry No Amide Reaction Temperature(°C) Reaction Time(hr) Yield (percent)a 15 70 5 93 16 70 5 83 17 70 5 >99 18 80 10 95 19 100 15 95b 20 100 5 93 21 80 10 97 22 100 5 87 23 90 5 94 24 60 5 91 25 80 5 89h 26 60 3 >99b 80 +3 27 50 5 87 28 50 5 96 a Isolation Yield b: Ammonium bromide was 10molpercent. Dichloromethane and 1 M hydrochloric acid aqueous solution were added to the reaction mixture for separation with separatory funnel. The aqueous layer was basified with sodium hydroxide aqueous solution, followed by the extraction of the target amine with ether. The organic layer was dried over sodium sulfate, and then the solvent was removed by rotary evaporation to obtain a yellow liquid product. Yield 119 mg (88percent). 1H NMR (400 MHz, CDCl3) δ 7.54-7.48 (m, 2H), 7.34 (t, J= 7.6 Hz, 2H), 7.22 (t, J= 7.6 Hz, 1H), 1.60 (br, 2H), 1.50 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 150.18, 128.16, 126.14, 124.57, 52.35, 32.69.

With NH4Br, ethylenediamine, Time= 10h, T= 100 °C , Microwave irradiation Patent; Kyushu University, National University Corporation; OHSHIMA Takashi; MORIMOTO Hiroyuki; SHIMIZU Yuhei; EP2821389; (2015); (A1) English View in Reaxys

O OH N H

H 2N

Rx-ID: 39286936 View in Reaxys 3/30 Yield

Conditions & References General Procedure for the rearrangement of free aromatic hydroxamic acids to anilines in the presence of a catalytic amount of acetic anhydride: General procedure: To a mixture of N-hydroxy-3-phenylpropanamide (1j) (0.198 g, 1.2 mmol), K2CO3 (0.166 g, 1.2 mmol), and DMSO (0.5 mL) was added acetic anhydride (1.1 mL, 0.012 mmol) and heated to 50 °C. After stirring at that temperature for 10 min,the reaction mixture was cooled to 0 °C and then treated with 2 M HCl (ca. 1mL). After the mixture became the clear solution, 2 M NaOH (ca. 2 mL) and di-t-butyl dicarbonate (0.55 mL, 2.4 mmol) was added successively. After stirring for 12 h, the mixture was extracted with Et2O (15 mL x 3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/Et2O,1:1) to yield t-butyl 3-phenylpropylcarbamate (2j) (0.122 g, 46percent) as a colorless liquid.

Stage 1: With acetic anhydride, potassium carbonate in dimethyl sulfoxide, Time= 24h, T= 50 °C , Lossen Rearrangement Stage 2: With hydrogenchloride in water, dimethyl sulfoxide, T= 0 °C Hoshino, Yujiro; Shimbo, Yuki; Ohtsuka, Naoya; Honda, Kiyoshi; Tetrahedron Letters; vol. 56; nb. 5; (2015); p.

710 - 712 View in Reaxys

HO

H 2N

Rx-ID: 1050150 View in Reaxys 4/30 Yield

Conditions & References With potassium cyanide, sulfuric acid in anhydrous butyl ether, T= 60 - 80 °C Christol,H. et al.; Bulletin de la Societe Chimique de France; (1961); p. 2319 - 2324 View in Reaxys

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Reaction Steps: 2 1: 95 percent / LiAlH4 / diethyl ether / 18 h / 0 - 20 °C With lithium aluminium tetrahydride in diethyl ether Metallinos, Costa; Nerdinger, Sven; Snieckus, Victor; Organic Letters; vol. 1; nb. 8; (1999); p. 1183 - 1186 View in Reaxys Reaction Steps: 2 1: NaN3; TFA / CHCl3 / 12 h / 20 °C 2: 19.8 g / H2 / Lindlar's catalyst / ethanol / 12 h With sodium azide, hydrogen, trifluoroacetic acid, Lindlar's catalyst in ethanol, chloroform Blanchet, Jerome; Macklin, Todd; Ang, Patrick; Metallinos, Costa; Snieckus, Victor; Journal of Organic Chemistry; vol. 72; nb. 9; (2007); p. 3199 - 3206 View in Reaxys Reaction Steps: 2 1: sodium azide, trifluoracetic acid / CHCl3 / 15 h / 5 - 20 °C 2: lithiumaluminium hydride / diethyl ether / 3 h / Ambient temperature With lithium aluminium tetrahydride, sodium azide, trifluoroacetic acid in diethyl ether, chloroform Aelterman, Wim; Tehrani, Kourosch Abbaspour; Coppens, Wim; Huybrechts, Tom; De Kimpe, Norbert; Tourwe, Dirk; Declercq, Jean-Paul; European Journal of Organic Chemistry; nb. 1; (1999); p. 239 - 250 View in Reaxys Reaction Steps: 2 1: 57 percent / PBr3 / CHCl3 / 2 h / 40 °C 2: 53 percent / liquid ammonia With ammonia, phosphorus tribromide in chloroform Kamer, Paul C. J.; Nolte, Roeland J. M.; Drenth, Wiendelt; Journal of the American Chemical Society; vol. 110; nb.

20; (1988); p. 6818 - 6825 View in Reaxys Reaction Steps: 2 1: sodium azide, 57percent aq. H2SO4 / CHCl3 / 48 h / ice-bath 2: 68 percent / lithium aluminum hydride / diethyl ether / 1.) 12 h, 2.) reflux, 1 h With lithium aluminium tetrahydride, sodium azide, sulfuric acid in diethyl ether, chloroform Timberlake, Jack W.; Alender, Jeff; Garner, Archie W.; Hodges, Melvin L.; Oezmeral, Cenan; et al.; Journal of Organic Chemistry; vol. 46; nb. 10; (1981); p. 2082 - 2089 View in Reaxys Reaction Steps: 2 1: HN3, CCl3CO2H / CHCl3 2: LiAlH4 / diethyl ether / Heating With lithium aluminium tetrahydride, tris-(2-chloro-ethyl)-amine, trichloroacetic acid in diethyl ether, chloroform Abramovitch,R.A.; Kyba,E.P.; Journal of the American Chemical Society; vol. 96; (1974); p. 480 - 488 View in Reaxys Reaction Steps: 2 1: sodium azide; trifluoroacetic acid / chloroform / -10 - 20 °C / Inert atmosphere 2: hydrogen / ethanol / 12 h With sodium azide, hydrogen, trifluoroacetic acid in ethanol, chloroform Schneider, Cedric; Broda, Ellen; Snieckus, Victor; Organic Letters; vol. 13; nb. 14; (2011); p. 3588 - 3591 View in Reaxys

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2H

N

2H 2H

2

H

2H

2H

H 2N

N

N

2H

2

H

2H

2

H

2H

2

H

Rx-ID: 2847620 View in Reaxys 5/30 Yield

Conditions & References

44.3 %

With lithium aluminium tetrahydride in diethyl ether, Time= 4h, Heating Leffler, J. E.; Zupancic, J. J.; Journal of the American Chemical Society; vol. 102; nb. 1; (1980); p. 259 - 267 View in Reaxys

Li

N

H 2N

Rx-ID: 10136689 View in Reaxys 6/30 Yield 90 %

Conditions & References With cerium(III) chloride Engel; Pan; Ying; Alemany; Journal of the American Chemical Society; vol. 123; nb. 16; (2001); p. 3706 - 3715 View in Reaxys

Mg Cl

Cl

N

H

H 2N

Rx-ID: 25927921 View in Reaxys 7/30 Yield 44 %

Conditions & References Stage 1: With titanium(IV) isopropylate in diethyl ether, T= 20 °C Stage 2: With hydrogenchloride in diethyl ether, dichloromethane, Further stages.

Tomashenko; Sokolov; Tomashevskii; Potekhin; De Meijere; Russian Journal of Organic Chemistry; vol. 43; nb.

10; (2007); p. 1421 - 1426 View in Reaxys

Br

H 2N

Rx-ID: 1981347 View in Reaxys 8/30 Yield 53 %

Conditions & References With ammonia Kamer, Paul C. J.; Nolte, Roeland J. M.; Drenth, Wiendelt; Journal of the American Chemical Society; vol. 110; nb.

20; (1988); p. 6818 - 6825 View in Reaxys With ammonia Jozwiak, Andrzej; Brzezinski, Jacek Z.; Plotka, Mieczyslaw W.; Szczesniak, Aleksandra K.; Malinowski, Zbigniew; Epsztajn, Jan; European Journal of Organic Chemistry; nb. 15; (2004); p. 3254 - 3261 View in Reaxys

H 2N

Rx-ID: 20583326 View in Reaxys 9/30 Yield

Conditions & References Reaction Steps: 2 1: NaN3, Cl3CCOOH / CHCl3 / 2 h / Heating 2: 61.5 percent / LiAlH4 / diethyl ether / 4 h / Heating With lithium aluminium tetrahydride, sodium azide, trichloroacetic acid in diethyl ether, chloroform

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Leffler, J. E.; Zupancic, J. J.; Journal of the American Chemical Society; vol. 102; nb. 1; (1980); p. 259 - 267 View in Reaxys Reaction Steps: 2 2: aq. NaOH / H2O With sodium hydroxide in water Kornblum, Nathan; Fifolt, Michael J.; Tetrahedron; vol. 45; nb. 5; (1989); p. 1311 - 1322 View in Reaxys

O

N

H 2N

O

Rx-ID: 5322655 View in Reaxys 10/30 Yield

Conditions & References

97 % Chro- With potassium hydroxide, nickel in ethanol, T= 20 °C , pH= 13, Electrolysis, Reduction mat., 2 % Chan-Shing, Elisa Soazara; Boucher, Denys; Lessard, Jean; Canadian Journal of Chemistry; vol. 77; nb. 5-6; Chromat.

(1999); p. 687 - 694 View in Reaxys

CBrCl3 H 2N

Rx-ID: 22507457 View in Reaxys 11/30 Yield

Conditions & References Reaction Steps: 2 1: aq. H2SO4 2: (alkaline hydrolysis) With sulfuric acid Kornblum,N. et al.; Journal of Organic Chemistry; vol. 43; nb. 7; (1978); p. 1394 - 1399 View in Reaxys Reaction Steps: 2 1: NaN3, CF3CO2H / CHCl3 2: Raney-Ni / propan-2-ol With sodium azide, trifluoroacetic acid, nickel in chloroform, isopropyl alcohol Balderman,D.; Kalir,A.; Synthesis; (1978); p. 24 - 26 View in Reaxys

O NH 2

H 2N

Rx-ID: 306624 View in Reaxys 12/30 Yield

Conditions & References With bromine Brander; Recueil des Travaux Chimiques des Pays-Bas; vol. 37; (1918); p. 83 View in Reaxys Baker; Ingold; Journal of the Chemical Society; (1927); p. 262 View in Reaxys With alkaline aqueous sodium hypobromite Cope; Foster; Towle; Journal of the American Chemical Society; vol. 71; (1949); p. 3929,3933 View in Reaxys

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N

O

H 2N

Rx-ID: 2163984 View in Reaxys 13/30 Yield

Conditions & References

72 %

With hydrogenchloride in water, 70-80 deg C, 0.5 h; reflux, 0.5 h Sato, Kazuo; Honma, Toyokuni; Sugai, Soji; Agricultural and Biological Chemistry; vol. 49; nb. 12; (1985); p. 3563 - 3568 View in Reaxys

Mg Br

N

H 2N

Rx-ID: 29053453 View in Reaxys 14/30 Yield

Conditions & References Stage 1: in tetrahydrofuran, diethyl ether, Time= 0.166667h, T= 100 °C , Microwave irradiation, Double Grignard addition Stage 2: With titanium(IV) isopropylate in tetrahydrofuran, diethyl ether, Time= 1h, T= 50 °C , Microwave irradiation, Double Grignard addition Wang, Ruifang; Gregg, Brian T.; Zhang, Wei; Golden, Kathryn C.; Quinn, John F.; Cui, Peng; Tymoshenko, Dmytro O.; Tetrahedron Letters; vol. 50; nb. 50; (2009); p. 7070 - 7073 View in Reaxys Stage 1: in diethyl ether, Time= 0.5h, T= 20 °C , Inert atmosphere Stage 2: With titanium(IV) isopropylate in diethyl ether, Time= 10h, Inert atmosphere Gorla, Suresh Kumar; Kavitha, Mandapati; Zhang, Minjia; Liu, Xiaoping; Sharling, Lisa; Gollapalli, Deviprasad R.; Striepen, Boris; Hedstrom, Lizbeth; Cuny, Gregory D.; Journal of Medicinal Chemistry; vol. 55; nb. 17; (2012); p. 7759 - 7771 View in Reaxys

NH

O

H 2N

Rx-ID: 1221706 View in Reaxys 15/30 Yield

Conditions & References With potassium hydroxide in ethylene glycol Duismann,W.; Ruechardt,C.; Chemische Berichte; vol. 106; (1973); p. 1083 - 1098 View in Reaxys (alkaline hydrolysis) Kornblum,N. et al.; Journal of Organic Chemistry; vol. 43; nb. 7; (1978); p. 1394 - 1399 View in Reaxys With sodium hydroxide in water Kornblum, Nathan; Fifolt, Michael J.; Tetrahedron; vol. 45; nb. 5; (1989); p. 1311 - 1322 View in Reaxys 2H

H 2N

H 2N

2

H

Rx-ID: 9416731 View in Reaxys 16/30

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Yield

Conditions & References With deuterium, cycloocta-1,5-dienyl Ir 1,1,1,5,5,5-hexa-fluoro-pentane-2,4-dionate in N,N-dimethyl-formamide, Time= 4h, T= 20 °C Hickey, Michael J.; Jones, John R.; Kingston, Lee P.; Lockley, William J. S.; Mather, Andrew N.; McAuley, Barry M.; Wilkinson, David J.; Tetrahedron Letters; vol. 44; nb. 20; (2003); p. 3959 - 3961 View in Reaxys With water-d2, [Ir(acetylacetonate)(1,5-cyclooctadiene)] in N,N-dimethyl acetamide, Time= 2.25h, T= 90 °C , Product distribution, Further Variations: Catalysts, Temperatures, microwave irradiation; reaction times McAuley; Hickey; Kingston; Jones; Lockley; Mather; Spink; Thompson; Wilkinson; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 46; nb. 13; (2003); p. 1191 - 1204 View in Reaxys With deuterium, (1,5-COD)Ir(I)-1,1,1,5,5,5-hexafluoropentan-2,4-dionate in N,N-dimethyl acetamide, Time= 4h, T= 20 °C Garman; Hickey; Kingston; McAuley; Jones; Lockley; Mather; Wilkinson; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 48; nb. 1; (2005); p. 75 - 84 View in Reaxys

Mg Cl

N

H 2N

Rx-ID: 10529159 View in Reaxys 17/30 Yield

Conditions & References

44 %

With titanium(IV) isopropylate in diethyl ether, Time= 10h, Heating Tomashenko, Olesya; Sokolov, Viktor; Tomashevskiy, Alexander; De Meijere, Armin; Synlett; nb. 4; (2007); p.

652 - 654 View in Reaxys

H 2N

H 2N

Rx-ID: 1127311 View in Reaxys 18/30 Yield

Conditions & References With hydrogenchloride, aluminium trichloride in toluene Kovacic,P. et al.; Journal of Organic Chemistry; vol. 33; (1968); p. 4515 - 4520 View in Reaxys

H 2N

Rx-ID: 22517845 View in Reaxys 19/30 Yield

Conditions & References Reaction Steps: 2 1: NCl3, AlCl3, tBuBr / 1,2-dichloro-ethane 2: AlCl3, HCl / toluene With hydrogenchloride, aluminium trichloride, nitrogen trichloride, 1-bromo-1,1-dimethylethane in 1,2-dichloro-ethane, toluene Kovacic,P. et al.; Journal of Organic Chemistry; vol. 33; (1968); p. 4515 - 4520 View in Reaxys

Cl

Cl Ce

H 2N

N

(v3)

O

H 2N

Rx-ID: 4776213 View in Reaxys 20/30

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Yield

Conditions & References

73 %

Time= 2h, T= -78 - 0 °C , 5.0 equival. MeCeCl2 Calderwood, David J.; Davies, Roy V.; Rafferty, Paul; Twigger, Helen L.; Whelan, Helen M.; Tetrahedron Letters; vol. 38; nb. 7; (1997); p. 1241 - 1244 View in Reaxys

Cl

H 2N

Cl Ce

N

(v3)

S

H 2N

Rx-ID: 4785631 View in Reaxys 21/30 Yield

Conditions & References

68 %

Time= 2h, T= -78 - 0 °C , 5.0 equival. MeCeCl2 Calderwood, David J.; Davies, Roy V.; Rafferty, Paul; Twigger, Helen L.; Whelan, Helen M.; Tetrahedron Letters; vol. 38; nb. 7; (1997); p. 1241 - 1244 View in Reaxys

Br Mg

H 2N

Rx-ID: 16750580 View in Reaxys 22/30 Yield

Conditions & References Reaction Steps: 3 1: diethyl ether / 1 h / Ambient temperature 2: sodium azide, trifluoracetic acid / CHCl3 / 15 h / 5 - 20 °C 3: lithiumaluminium hydride / diethyl ether / 3 h / Ambient temperature With lithium aluminium tetrahydride, sodium azide, trifluoroacetic acid in diethyl ether, chloroform Aelterman, Wim; Tehrani, Kourosch Abbaspour; Coppens, Wim; Huybrechts, Tom; De Kimpe, Norbert; Tourwe, Dirk; Declercq, Jean-Paul; European Journal of Organic Chemistry; nb. 1; (1999); p. 239 - 250 View in Reaxys

11-chloro-1-isopropyl-benzene H 2N

Rx-ID: 6075256 View in Reaxys 23/30 Yield

Conditions & References With ammonia, T= 20 °C Brander; Recueil des Travaux Chimiques des Pays-Bas; vol. 37; (1918); p. 83 View in Reaxys

Z N NH

NH

H N

O

N

HO O

N

O O

N

O

E

O

H 2N

NH

Rx-ID: 10274183 View in Reaxys 24/30 Yield

Conditions & References With sodium methylate, T= 75 °C Shao, Ning; Wang, Cheng; Huang, Xianhai; Xiao, Dong; Palani, Anandan; Aslanian, Robert; Shih, Neng-Yang; Tetrahedron Letters; vol. 47; nb. 38; (2006); p. 6743 - 6746 View in Reaxys

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β-nitro-β-phenyl-propane H 2N

Rx-ID: 6075255 View in Reaxys 25/30 Yield

Conditions & References With ethanol, acetic acid, zinc Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 26; (1894); p. 84; Chem. Zentralbl.; vol. 65; nb. II; (1894); p. 33 View in Reaxys With hydrogenchloride, tin, ethanol Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 26; (1894); p. 84; Chem. Zentralbl.; vol. 65; nb. II; (1894); p. 33 View in Reaxys

S

Li

N

H 2N

Rx-ID: 1244389 View in Reaxys 26/30 Yield

Conditions & References (i) Et2O, (ii) H2O, Multistep reaction Davis,F.A.; Mancinelli,P.A.; Journal of Organic Chemistry; vol. 42; nb. 2; (1977); p. 398 - 399 View in Reaxys

H 2N

O H

O

H N

NH

O

H

H 2N

O

O

O

NH NH 2

NH 2

H 2N

Rx-ID: 7919930 View in Reaxys 27/30 Yield

Conditions & References T= 180 - 185 °C Brander; Recueil des Travaux Chimiques des Pays-Bas; vol. 37; (1918); p. 83 View in Reaxys

alkali

Br Br O

H 2N

NH 2

Rx-ID: 7448451 View in Reaxys 28/30 Yield

Conditions & References Brander; Recueil des Travaux Chimiques des Pays-Bas; vol. 37; (1918); p. 83 View in Reaxys

O

O

OH

zinc dust

N

O

O

H 2N

Rx-ID: 7448452 View in Reaxys 29/30 Yield

Conditions & References Konowalow; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 26; (1894); p. 84; Chem. Zentralbl.; vol. 65; nb. II; (1894); p. 33 View in Reaxys

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H 2N

Rx-ID: 6075254 View in Reaxys 30/30 Yield

Conditions & References Lindberg et al.; Acta Pharmaceutica Suecica; vol. 6; (1969); p. 617,620 View in Reaxys Sugi; Mitsui; Bulletin of the Chemical Society of Japan; vol. 42; (1969); p. 2984,2988 View in Reaxys Schik et al.; Azerbaidzhanskii Khimicheskii Zhurnal; vol. 1; (1974); p. 23; ; vol. 81; nb. 104882; (1974) View in Reaxys Alvernhe; Laurent; Tetrahedron Letters; (1973); p. 1057,1058 View in Reaxys 6 : Preparation of α,α-Dimethylbenzylamine (DMBA) EXAMPLE 6 Preparation of α,α-Dimethylbenzylamine (DMBA) A mixture of 125 g of MDBC prepared according to Example 5 and 500 g of 85percent potassium hydroxide in 270 ml of methyl cellosolve was heated at reflux temperature for 4 hours.

The mixture was then cooled and mixed with 500 ml of methylene chloride and 300 ml of water.

The methylene chloride layer was separated and washed with water until its volume remained constant.

The methylene chloride layer was dried over potassium carbonate and distilled. α,α-Dimethylbenzylamine, 67 g, was collected; bp 95°-6° C./22 mm Hg; IR (cm-1): 3340, 3270, 2950, 1600, 760, 795.

Patent; Cytec Technology Corp.; US5840908; (1998); (A1) English View in Reaxys

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