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33 reactions in Reaxys
2018-06-23 11h:28m:56s (UTC)
H 2N
1. Query
Search as: Product, As drawn, No mixtures ) AND (RX.PRO='phentermin'))
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OH H 2N
H 2N
Rx-ID: 393643 View in Reaxys 1/33 Yield
Conditions & References
41 %
1 : Synthesis of 1e P (677 mg, 22 mmol) was slowly added to the solution of ld (1.5 g, 9.1 mmol) in HI (22 mE 45percent in water) at room temperature. The mixture was stirred at 135° C. overnight, and then cooled to room temperature. Water (100 mE) was added to the above mixture, which was filtered. Saturated aqueous Na25203 solution (100 mE) was added to the filtrate and was made basic with 40percent NaOH (20 mE). The resulting mixture was extracted with ethyl acetate (100 mEx3). The combined ethyl acetate layer was washed with water and dried over anhydrous Na2504 and evaporated. The residue was purified by silica column chromatography (DCM: MeOH30:1, v:v) to provide R’ (0.55 g, 41percent yield). With phosphorus, hydrogen iodide in water, T= 135 °C Patent; HELSINN HEALTHCARE SA; Giuliano, Claudio; Daina, Antoine; Pietra, Claudio; (254 pag.); US2017/275301; (2017); (A1) English View in Reaxys With phosphorus, hydrogen iodide Zenitz; Macks; Moore; Journal of the American Chemical Society; vol. 70; (1948); p. 955 View in Reaxys
H N
Cl
H 2N
O
Rx-ID: 8622327 View in Reaxys 2/33 Yield
Conditions & References With acetic acid, thiourea in ethanol, Time= 10h, Heating, Substitution Jirgensons; Kauss; Kalvinsh; Gold; Synthesis; nb. 12; (2000); p. 1709 - 1712 View in Reaxys 5.D :A mixture of the chloroacetamide from Step C above (12.2 g, 54.2 mmol), thiourea (2.7 g, 65 mmol) and acetic acid (10.6 mL, 0.325 mol) in absolute ethanol (60 mL) was heated to reflux to 16 h. The reaction mixture was then diluted with water (50 mL) and extracted with EtOAc (2*75 mL). The combined organic fractions were washed with brine (5*50 mL), dried over MgSO4 and evaporated in vacuo. Distillation under high vacuum provided the free amine (bp 125° C.at;6 Torr). This crude material was dissolved in Et&2O
and 4 mL of 4N HCl in 1,4-dioxane was added.
Filtration of the white precipitate provided the desired compound as its hydrochloric acid salt. With acetic acid, thiourea in ethanol, Time= 16h, Heating / reflux Patent; Andersen, Denise Lyn; Chang, Catherine H.; Falsey, James R.; Frohn, Michael J.; Hong, Fang-Tsao; Liao, Hongyu; Liu, Longbin; Lopez, Patricia; Retz, Daniel Martin; Rishton, Gilbert M.; Rzasa, Robert M.; Siegmund, Aaron; Tadesse, Seifu; Tamayo, Nuria; Tegley, Christopher M.; US2006/69110; (2006); (A1) English View in Reaxys With acetic acid, thiourea in ethanol, Time= 10h, T= 80 °C Yuan, Ming; Chen, Li; Wang, Junwei; Chen, Shenjie; Wang, Kongchao; Xue, Yongbo; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui; Organic Letters; vol. 17; nb. 2; (2015); p. 346 - 349 View in Reaxys 0.567 g
With acetic acid, thiourea in ethanol, Time= 10h, Reflux
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Mancinelli, Andrea; Alamillo, Carla; Albert, Joan; Ariza, Xavier; Etxabe, Haizea; Farràs, Jaume; Garcia, Jordi; Granell, Jaume; Quijada, F. Javier; Organometallics; vol. 36; nb. 4; (2017); p. 911 - 919 View in Reaxys
HO
H 2N
Rx-ID: 15714823 View in Reaxys 3/33 Yield
Conditions & References Reaction Steps: 2 1: 78 percent / AcOH; H2SO4 / 5 h / 20 °C 2: thiourea; AcOH / ethanol / 10 h / Heating With sulfuric acid, acetic acid, thiourea in ethanol, 1: Ritter reaction / 2: Substitution Jirgensons; Kauss; Kalvinsh; Gold; Synthesis; nb. 12; (2000); p. 1709 - 1712 View in Reaxys Reaction Steps: 3 1: 79 percent / H2SO4, AcOH / Ambient temperature; The reagents were added at 0 gradC, then stirring overnight at room temperature. 2: 1. 20percent NaOH, 2. HCl gas / 1.220 gradC, 24h; 3: by neutralization With hydrogenchloride, sodium hydroxide, sulfuric acid, acetic acid Dube, Michael F.; Timberlake, Jack W.; Tetrahedron; vol. 36; (1980); p. 1753 - 1756 View in Reaxys Reaction Steps: 2 1: 15.2 g / H2SO4 / acetic acid / 12 h / Ambient temperature 2: aq. KOH / 24 h / 200 °C With potassium hydroxide, sulfuric acid in acetic acid 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: acetic acid; sulfuric acid 2: aq. NaOH solution With sodium hydroxide, sulfuric acid, acetic acid Ritter; Kalish; Journal of the American Chemical Society; vol. 70; (1948); p. 4048; Organic Syntheses; vol. 44; (1964); p. 44,45 View in Reaxys Reaction Steps: 2 1.1: sulfuric acid; acetic acid / 20 - 65 °C 1.2: pH > 11 2.1: potassium hydroxide / ethylene glycol / 8 h / Reflux With sulfuric acid, acetic acid, potassium hydroxide in ethylene glycol Patent; Pathway Therapeutics Inc.; US2012/252802; (2012); (A1) English View in Reaxys Reaction Steps: 2 1: trifluoroacetic acid / 9 h / 50 °C 2: thiourea; acetic acid / ethanol / 10 h / 80 °C With acetic acid, thiourea, trifluoroacetic acid in ethanol Yuan, Ming; Chen, Li; Wang, Junwei; Chen, Shenjie; Wang, Kongchao; Xue, Yongbo; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui; Organic Letters; vol. 17; nb. 2; (2015); p. 346 - 349
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View in Reaxys Reaction Steps: 2 1: sulfuric acid; acetic acid / 0 - 20 °C 2: acetic acid; thiourea / ethanol / 10 h / Reflux With sulfuric acid, acetic acid, thiourea in ethanol, 1: |Ritter Amidation Mancinelli, Andrea; Alamillo, Carla; Albert, Joan; Ariza, Xavier; Etxabe, Haizea; Farràs, Jaume; Garcia, Jordi; Granell, Jaume; Quijada, F. Javier; Organometallics; vol. 36; nb. 4; (2017); p. 911 - 919 View in Reaxys
H 2N
H
O
Rx-ID: 46359128 View in Reaxys 4/33 Yield
Conditions & References Reaction Steps: 3 1: sodium methylate / methanol / 20 °C 2: zinc; hydrogenchloride / ethanol; water / 4 h / 70 °C 3: hydrogen iodide; phosphorus / water / 135 °C With hydrogenchloride, phosphorus, hydrogen iodide, sodium methylate, zinc in methanol, ethanol, water Patent; HELSINN HEALTHCARE SA; Giuliano, Claudio; Daina, Antoine; Pietra, Claudio; (254 pag.); US2017/275301; (2017); (A1) English View in Reaxys HO
O
H 2N
N O
Rx-ID: 46359182 View in Reaxys 5/33 Yield
Conditions & References Reaction Steps: 2 1: zinc; hydrogenchloride / ethanol; water / 4 h / 70 °C 2: hydrogen iodide; phosphorus / water / 135 °C With hydrogenchloride, phosphorus, hydrogen iodide, zinc in ethanol, water Patent; HELSINN HEALTHCARE SA; Giuliano, Claudio; Daina, Antoine; Pietra, Claudio; (254 pag.); US2017/275301; (2017); (A1) English View in Reaxys
H 2N
HO
O
Rx-ID: 39305530 View in Reaxys 6/33 Yield
Conditions & References Reaction Steps: 4 1: sulfuric acid / 50 °C 2: tetrahydrofuran / 2 h / 0 - 25 °C 3: trifluoroacetic acid / 9 h / 50 °C 4: thiourea; acetic acid / ethanol / 10 h / 80 °C With sulfuric acid, acetic acid, thiourea, trifluoroacetic acid in tetrahydrofuran, ethanol Yuan, Ming; Chen, Li; Wang, Junwei; Chen, Shenjie; Wang, Kongchao; Xue, Yongbo; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui; Organic Letters; vol. 17; nb. 2; (2015); p. 346 - 349 View in Reaxys
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H 2N
O
O
Rx-ID: 39305535 View in Reaxys 7/33 Yield
Conditions & References Reaction Steps: 3 1: tetrahydrofuran / 2 h / 0 - 25 °C 2: trifluoroacetic acid / 9 h / 50 °C 3: thiourea; acetic acid / ethanol / 10 h / 80 °C With acetic acid, thiourea, trifluoroacetic acid in tetrahydrofuran, ethanol Yuan, Ming; Chen, Li; Wang, Junwei; Chen, Shenjie; Wang, Kongchao; Xue, Yongbo; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui; Organic Letters; vol. 17; nb. 2; (2015); p. 346 - 349 View in Reaxys
O
H N
H 2N
Rx-ID: 2086324 View in Reaxys 8/33 Yield 66 %
Conditions & References With potassium hydroxide in water, Time= 24h, T= 220 °C Wannagat, U.; Damrath, V.; Harder, U.; Monatshefte fuer Chemie; vol. 125; nb. 11; (1994); p. 1159 - 1170 View in Reaxys With potassium hydroxide, Time= 24h, T= 200 °C 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: 1. 20percent NaOH, 2. HCl gas / 1.220 gradC, 24h; 2: by neutralization With hydrogenchloride, sodium hydroxide Dube, Michael F.; Timberlake, Jack W.; Tetrahedron; vol. 36; (1980); p. 1753 - 1756 View in Reaxys With potassium hydroxide in ethylene glycol, Reflux Hoenke, Christoph; Bouyssou, Thierry; Tautermann, Christofer S.; Rudolf, Klaus; Schnapp, Andreas; Konetzki, Ingo; Bioorganic and Medicinal Chemistry Letters; vol. 19; nb. 23; (2009); p. 6640 - 6644 View in Reaxys 13 :To a mixture of 2-methyl-1-phenyl-2-propanol (1.5 g, 10 mmol) and acetonitrile (3 mL) in acetic acid (15 mL) was added concentrated sulfuric acid (3 mL) dropwise at room temperature. The mixture was stirred at 65° C. for 3 hours and then poured into ice-water (ca. 200 mL). The aqueous solution was basified with saturated aqueous sodium hydroxide until pH>11. The suspension was stirred for further 0.5 hour, and then the precipitated solid was filtered and washed with water. The white solid was air-dried to give N-(2-methyl-1-phenylpropan-2-yl)acetamide (1.5 g, 78percent yield), which was used for the next step without further purification.A mixture of N-(2-methyl-1-phenylpropan-2-yl)acetamide (191 mg, 1.00 mmol) and potassium hydroxide (1 g) in ethylene glycol (10 mL) was refluxed for 8 hours. The mixture was diluted with ice-water and extracted with ethyl acetate. The combined organic fractions were washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude 2-methyl-1-phenylpropan-amine (200 mg) as a brown oil, which was used for the next step without further purification.Compound A14 was synthesized according to the procedure for compound A22, substituting the crude 2-methyl-1-phenylpropan-amine in place of 1-(4-fluorophenyl)-2-methylpropan-2-amine. The product was purified by preparative HPLC to give compound A14 (30 mg, 13percent yield for 2 steps) as a white solid: 96.4percent purity (HPLC); MS m/z: 480.3 (M+1); 1H NMR (CDCl3, 500 MHz) δ 8.39 (d, J=7.5 Hz, 1H), 7.90 (d, J=7.5 Hz, 1H), 7.65 (t, JHF=54.0 Hz, 1H), 7.42 (m, 2H), 7.28 (m, 3H), 7.16-7.10 (m, 2H), 5.15 (s, 1H), 4.01-3.75 (m, 8H), 3.22 (s, 2H), 1.49 (s, 6H) ppm.
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Stage 1: With potassium hydroxide in ethylene glycol, Time= 8h, Reflux Stage 2: With water Patent; Pathway Therapeutics Inc.; US2012/252802; (2012); (A1) English View in Reaxys
H 2N
O N O
Rx-ID: 2086949 View in Reaxys 9/33 Yield 98 %
Conditions & References With 10% palladium on activated charcoal, hydrogen in methanol, Time= 24h, T= 40 °C Gildner, Peter G.; Gietter, Amber A. S.; Cui, Di; Watson, Donald A.; Journal of the American Chemical Society; vol. 134; nb. 24; (2012); p. 9942 - 9945 View in Reaxys
79 %
With phosphate buffer, potassium chloride in ethanol, T= 30 °C , cotrolled potential electrolysis, cathod: Hg, vs. SCE Ohmori, Hidenobu; Furusako, Shoji; Kashu, Mieko; Ueda, Chihiro; Masui, Masaichiro; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3345 - 3353 View in Reaxys Reaction Steps: 2 1: 98 percent / citrate buffer (pH 4.2), KCl / ethanol / 30 °C / cotrolled potential electrolysis, cathod: Hg, vs. S.C.E. 2: 57 percent / citrate buffer (pH 4.0), KCl / ethanol / 30 °C / cotrolled potential electrolysis, cathod: Hg, vs. SCE With citrate buffer, potassium chloride in ethanol Ohmori, Hidenobu; Furusako, Shoji; Kashu, Mieko; Ueda, Chihiro; Masui, Masaichiro; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3345 - 3353 View in Reaxys
H 2N
Br
Rx-ID: 33530902 View in Reaxys 10/33 Yield
Conditions & References Reaction Steps: 2 1: 2-(2,6-dimethylphenyl)amine-4-(2,6-dimethylphenyl)imine-2-pentene; copper(I) bromide; sodium t-butanolate / cyclohexane / 48 h / 60 °C / Inert atmosphere 2: 10% palladium on activated charcoal; hydrogen / methanol / 24 h / 40 °C With 2-(2,6-dimethylphenyl)amine-4-(2,6-dimethylphenyl)imine-2-pentene, 10% palladium on activated charcoal, hydrogen, copper(I) bromide, sodium t-butanolate in methanol, cyclohexane Gildner, Peter G.; Gietter, Amber A. S.; Cui, Di; Watson, Donald A.; Journal of the American Chemical Society; vol. 134; nb. 24; (2012); p. 9942 - 9945 View in Reaxys
H 2N
H N S O
O
Rx-ID: 29701981 View in Reaxys 11/33
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Yield
Conditions & References With piperidine in N,N-dimethyl-formamide, T= 25 °C Ishibashi, Yoshitaka; Miyata, Kengo; Kitamura, Masato; European Journal of Organic Chemistry; nb. 22; (2010); p. 4201 4204 View in Reaxys
O
H 2N
H N
O
Rx-ID: 10246308 View in Reaxys 12/33 Yield
Conditions & References
99 % Spectr.
With trifluorormethanesulfonic acid, [CpRu(IV)(δ-C3H5)(2-quinolinecarboxylato)]PF6 in methanol, Time= 0.5h, T= 30 °C Tanaka, Shinji; Saburi, Hajime; Murase, Takanori; Yoshimura, Masahiro; Kitamura, Masato; Journal of Organic Chemistry; vol. 71; nb. 12; (2006); p. 4682 - 4684 View in Reaxys
O
H 2N
H N
P O O
Rx-ID: 8690702 View in Reaxys 13/33 Yield
Conditions & References With hydrogenchloride in tetrahydrofuran, water, Time= 168h, T= 20 °C Gajda; Koziara; Napieraj; Sikora; Zwierzak; Polish Journal of Chemistry; vol. 74; nb. 10; (2000); p. 1385 - 1387 View in Reaxys
H 2N O
O
Rx-ID: 24295807 View in Reaxys 14/33 Yield
Conditions & References 37 : EXAMPLE 37: EXAMPLE 37: Preparation of N-(2-Hydroxy-3-phenoxypropyl)-1,1-dimethyl-2-phenylethylamine Hydrochloride, Compound 56 STR37 Using the method of Example 5, supra, 1,2-epoxy-3-phenoxypropane (600 mg, 4 mmol) and 1,1-dimethyl-2-phenylethylamine (596 mg, 4 mmol) yielded the title compound: GC/EI-MS, m/z (rel. int.) 284 (M+1, 1), 208 (100), 162 (1), 133 (7), 91 (27), 77 (15), 70 (22). Patent; NPS Pharmaceuticals, Inc.; SmithKline Beecham, Corp.; SmithKline Beecham, PLC; US6022894; (2000); (A) English View in Reaxys
H 2N
Rx-ID: 6713021 View in Reaxys 15/33 Yield
Conditions & References Shetty; Journal of Organic Chemistry; vol. 26; (1961); p. 3002
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View in Reaxys Patent; Manufactures J.R.Bottu; FR1551268; (1968); ; vol. 72; nb. 12418s; (1970) View in Reaxys Marquardt; Edwards; The Journal of organic chemistry; vol. 37; nb. 11; (1972); p. 1861 - 1863 View in Reaxys Christol et al.; Bulletin de la Societe Chimique de France; (1961); p. 2317 View in Reaxys Patent; Wallace and Tiesnan; GB910789; (1963); ; vol. 59; nb. 2712; (1963) View in Reaxys STR61 TRANYLCYPROMINE ANILERIDINE PHENTERMINE Patent; University of Florida; US4771059; (1988); (A) English View in Reaxys
H 2N
H 2N
Cl 2
H
NH 2
Rx-ID: 2324675 View in Reaxys 16/33 Yield
Conditions & References With hydrogenchloride, phosphoric acid, sodium nitrite, 1.) MeOH, 3 h, reflux, water, Yield given. Multistep reaction Leclerc; Decker; Schwartz; Arzneimittel-Forschung/Drug Research; vol. 35; nb. 9; (1985); p. 1357 - 1367 View in Reaxys O
H 2N
O N N
O
O
Rx-ID: 19069256 View in Reaxys 17/33 Yield
Conditions & References Reaction Steps: 2 1: 1.) H2, 2.) HCl / 1.) 10percent Pd/C / 1.) ethanol, 8 h, reflux 2: 1.) NaNO2, 37percent HCl, 2.) H3PO4 / 1.) MeOH, 3 h, reflux, water With hydrogenchloride, phosphoric acid, hydrogen, sodium nitrite, 10 wt. % palladium on activated carbon Leclerc; Decker; Schwartz; Arzneimittel-Forschung/Drug Research; vol. 35; nb. 9; (1985); p. 1357 - 1367 View in Reaxys
H 2N
O N O
Cl
Rx-ID: 19077499 View in Reaxys 18/33 Yield
Conditions & References Reaction Steps: 3 1: 74 percent / Na, EtOH / 12 h / Heating 2: 1.) H2, 2.) HCl / 1.) 10percent Pd/C / 1.) ethanol, 8 h, reflux 3: 1.) NaNO2, 37percent HCl, 2.) H3PO4 / 1.) MeOH, 3 h, reflux, water With hydrogenchloride, ethanol, phosphoric acid, hydrogen, sodium, sodium nitrite, 10 wt. % palladium on activated carbon Leclerc; Decker; Schwartz; Arzneimittel-Forschung/Drug Research; vol. 35; nb. 9; (1985); p. 1357 - 1367 View in Reaxys
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H N
HO
H 2N
Rx-ID: 2102442 View in Reaxys 19/33 Yield 57 %
Conditions & References With citrate buffer, potassium chloride in ethanol, T= 30 °C , cotrolled potential electrolysis, cathod: Hg, vs. SCE Ohmori, Hidenobu; Furusako, Shoji; Kashu, Mieko; Ueda, Chihiro; Masui, Masaichiro; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 9; (1984); p. 3345 - 3353 View in Reaxys
H 2N
H 2N Cl
H
Rx-ID: 2427013 View in Reaxys 20/33 Yield
Conditions & References by neutralization Dube, Michael F.; Timberlake, Jack W.; Tetrahedron; vol. 36; (1980); p. 1753 - 1756 View in Reaxys O H N
N Cl
H
HO
O
OH H 2N
H N
HO
OH
HO
Rx-ID: 3491655 View in Reaxys 21/33 Yield
Conditions & References T= 37 °C , metabolism Dell; Donik; Jacobi; Kamp; Arzneimittel-Forschung/Drug Research; vol. 30; nb. 7; (1980); p. 1138 - 1144 View in Reaxys
H 2N Mg Cl
Rx-ID: 20861294 View in Reaxys 22/33 Yield
Conditions & References Reaction Steps: 4 1: 61 percent 2: 79 percent / H2SO4, AcOH / Ambient temperature; The reagents were added at 0 gradC, then stirring overnight at room temperature. 3: 1. 20percent NaOH, 2. HCl gas / 1.220 gradC, 24h; 4: by neutralization With hydrogenchloride, sodium hydroxide, sulfuric acid, acetic acid Dube, Michael F.; Timberlake, Jack W.; Tetrahedron; vol. 36; (1980); p. 1753 - 1756
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View in Reaxys O
H N
H 2N
Rx-ID: 377468 View in Reaxys 23/33 Yield
Conditions & References With sodium hydroxide Ritter; Kalish; Journal of the American Chemical Society; vol. 70; (1948); p. 4048; Organic Syntheses; vol. 44; (1964); p. 44,45 View in Reaxys With hydrogenchloride Moed et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 74; (1955); p. 919,922 View in Reaxys NH 2 H 2N
H 2N
Rx-ID: 387090 View in Reaxys 24/33 Yield
Conditions & References With hypophosphoric acid, sodium nitrite Hass; Bender; Journal of the American Chemical Society; vol. 71; (1949); p. 3482,3485 View in Reaxys
H 2N
H 2N
NH 2
Rx-ID: 455243 View in Reaxys 25/33 Yield
Conditions & References With hypophosphoric acid, sodium nitrite Kornblum; Iffland; Journal of the American Chemical Society; vol. 71; (1949); p. 2137,2138,2140 View in Reaxys O O
O
O N
H 2N
N
Rx-ID: 22082478 View in Reaxys 26/33 Yield
Conditions & References Reaction Steps: 2 1: Raney nickel; ethanol / 60 °C / 58840.6 Torr / Hydrogenation 2: aqueous hypophosphoric acid; sodium nitrite With ethanol, nickel, hypophosphoric acid, sodium nitrite Hass; Bender; Journal of the American Chemical Society; vol. 71; (1949); p. 3482,3485 View in Reaxys
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Cl H 2N
O N O
Rx-ID: 22106218 View in Reaxys 27/33 Yield
Conditions & References Reaction Steps: 3 1: sodium ethylate solution 2: Raney nickel; ethanol / 60 °C / 58840.6 Torr / Hydrogenation 3: aqueous hypophosphoric acid; sodium nitrite With ethanol, sodium ethanolate, nickel, hypophosphoric acid, sodium nitrite Hass; Bender; Journal of the American Chemical Society; vol. 71; (1949); p. 3482,3485 View in Reaxys Reaction Steps: 3 1: 2-nitro-propane; ethanolic sodium ethylate solution / 25 °C 2: Raney nickel; ethanol / 60 °C / 58840.6 Torr / Hydrogenation 3: aqueous hypophosphoric acid; sodium nitrite With ethanol, 2-nitropropane, sodium ethanolate, nickel, hypophosphoric acid, sodium nitrite Hass; Bender; Journal of the American Chemical Society; vol. 71; (1949); p. 3482,3485 View in Reaxys
H 2N
Rx-ID: 22034758 View in Reaxys 28/33 Yield
Conditions & References Reaction Steps: 2 1: acetic acid; sulfuric acid 2: aq. NaOH solution With sodium hydroxide, sulfuric acid, acetic acid Ritter; Kalish; Journal of the American Chemical Society; vol. 70; (1948); p. 4048; Organic Syntheses; vol. 44; (1964); p. 44,45 View in Reaxys
H 2N
Rx-ID: 22036057 View in Reaxys 29/33 Yield
Conditions & References Reaction Steps: 2 1: acetic acid; sulfuric acid 2: aq. NaOH solution With sodium hydroxide, sulfuric acid, acetic acid Ritter; Kalish; Journal of the American Chemical Society; vol. 70; (1948); p. 4048; Organic Syntheses; vol. 44; (1964); p. 44,45 View in Reaxys
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H 2N
2-amino-2-methyl-1-phenyl-propanol-(1)-hydrochloride
Rx-ID: 6713022 View in Reaxys 30/33 Yield
Conditions & References With thionyl chloride, beim Hydrieren des erhaltenen (+-)-2-Chlor-1.1-dimethyl-2-phenyl-aethylamin-hydrochlorids an Palladium in Aethanol Patent; Merrell Co.; US2408345; (1942) View in Reaxys
H 2N
H N
H N
O
Rx-ID: 327876 View in Reaxys 31/33 Yield
Conditions & References With calcium hydroxide, water, T= 230 °C Mentzer; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 213; (1941); p. 581,583 View in Reaxys
O
H 2N
N
Rx-ID: 22047352 View in Reaxys 32/33 Yield
Conditions & References Reaction Steps: 2 1: diethyl ether 2: calcium hydroxide; water / 230 °C With calcium hydroxide, diethyl ether, water Mentzer; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 213; (1941); p. 581,583 View in Reaxys
H 2N
H 2N
O
Rx-ID: 22053335 View in Reaxys 33/33 Yield
Conditions & References Reaction Steps: 2 1: aqueous potassium hypobromite 2: calcium hydroxide; water / 230 °C With calcium hydroxide, potassium hypobromite, water Mentzer; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 213; (1941); p. 581,583 View in Reaxys Reaction Steps: 3 1: aqueous potassium hypobromite 2: diethyl ether 3: calcium hydroxide; water / 230 °C
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With calcium hydroxide, potassium hypobromite, diethyl ether, water Mentzer; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 213; (1941); p. 581,583 View in Reaxys
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