2-Methyl-1-phenylpropan-2-amine (Phentermine) by Asch

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Reactions (44)

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Substances (3)

Citations (36)

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References

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Rx-ID: 8622327 Find similar reactions

With acetic acid; thiourea in ethanol

Substitution; 10 h; Heating;

Jirgensons; Kauss; Kalvinsh; Gold

Synthesis, 2000 , # 12 p. 1709 - 1712 Title/Abstract Full Text View citing articles Show Details

With acetic acid; thiourea in ethanol

16 h; Heating / reflux; Hide Experimental Procedure

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.

Patent: US2006/69110 A1, 2006 ; Location in patent: Page/Page column 16 ; Title/Abstract Full Text Show Details

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

T=80°C; 10 h;

Yuan, Ming; Chen, Li; Wang, Junwei; Chen, Shenjie; Wang, Kongchao; Xue, Yongbo; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui

Organic Letters, 2015 , vol. 17, # 2 p. 346 - 349 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 15714823 Find similar reactions

Multi-step reaction with 2 steps 1: 78 percent / AcOH; H2SO4 / 5 h / 20 °C 2: thiourea; AcOH / ethanol / 10 h / Heating View Scheme

Jirgensons; Kauss; Kalvinsh; Gold

Synthesis, 2000 , # 12 p. 1709 - 1712 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 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 View Scheme

Dube, Michael F.; Timberlake, Jack W.

Tetrahedron, 1980 , vol. 36, p. 1753 - 1756 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 15.2 g / H2SO4 / acetic acid / 12 h / Ambient temperature 2: aq. KOH / 24 h / 200 °C View Scheme

Timberlake, Jack W.; Alender, Jeff; Garner, Archie W.; Hodges, Melvin L.; Oezmeral, Cenan; et al.

Journal of Organic Chemistry, 1981 , vol. 46, # 10 p. 2082 - 2089 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid 2: aq. NaOH solution View Scheme

Ritter; Kalish

Journal of the American Chemical Society, 1948 , vol. 70, p. 4048 Organic Syntheses, 1964 , vol. 44, p. 44,45 Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1.1: sulfuric acid; acetic acid / 20 - 65 °C 1.2: pH > 11 2.1: potassium hydroxide / ethylene glycol / 8 h / Reflux View Scheme

Pathway Therapeutics Inc.

Patent: US2012/252802 A1, 2012 ;

Multi-step reaction with 2 steps 1: trifluoroacetic acid / 9 h / 50 °C 2: thiourea; acetic acid / ethanol / 10 h / 80 °C View Scheme

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Title/Abstract Full Text Show Details

Yuan, Ming; Chen, Li; Wang, Junwei; Chen, Shenjie; Wang, Kongchao; Xue, Yongbo; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui

Organic Letters, 2015 , vol. 17, # 2 p. 346 - 349 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 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 View Scheme

Rx-ID: 39305530 Find similar reactions

Yuan, Ming; Chen, Li; Wang, Junwei; Chen, Shenjie; Wang, Kongchao; Xue, Yongbo; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui

Organic Letters, 2015 , vol. 17, # 2 p. 346 - 349 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: tetrahydrofuran / 2 h / 0 - 25 °C 2: trifluoroacetic acid / 9 h / 50 °C 3: thiourea; acetic acid / ethanol / 10 h / 80 °C View Scheme

Rx-ID: 39305535 Find similar reactions

Yuan, Ming; Chen, Li; Wang, Junwei; Chen, Shenjie; Wang, Kongchao; Xue, Yongbo; Yao, Guangmin; Luo, Zengwei; Zhang, Yonghui

Organic Letters, 2015 , vol. 17, # 2 p. 346 - 349 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2086324 Find similar reactions

With potassium hydroxide in water

T=220°C; 24 h;

Wannagat, U.; Damrath, V.; Harder, U.

Monatshefte fuer Chemie, 1994 , vol. 125, # 11 p. 1159 - 1170 Title/Abstract Full Text View citing articles Show Details

With potassium hydroxide

T=200°C; 24 h;

Timberlake, Jack W.; Alender, Jeff; Garner, Archie W.; Hodges, Melvin L.; Oezmeral, Cenan; et al.

Journal of Organic Chemistry, 1981 , vol. 46, # 10 p. 2082 - 2089 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 1. 20percent NaOH, 2. HCl gas / 1.220 gradC, 24h; 2: by neutralization View Scheme

Dube, Michael F.; Timberlake, Jack W.

Tetrahedron, 1980 , vol. 36, p. 1753 - 1756 Title/Abstract Full Text View citing articles Show Details

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, 2009 , vol. 19, # 23 p. 6640 - 6644 Title/Abstract Full Text View citing articles Show Details

Stage #1: With potassium hydroxide in ethylene glycol

8 h; Reflux; Stage #2: With water

Pathway Therapeutics Inc.

Patent: US2012/252802 A1, 2012 ; Location in patent: Page/Page column 75 ;

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Title/Abstract Full Text Show Details

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-1phenylpropan-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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Rx-ID: 2086949 Find similar reactions

98%

With palladium on activated charcoal; hydrogen in methanol

T=40°C; 24 h;

Gildner, Peter G.; Gietter, Amber A. S.; Cui, Di; Watson, Donald A.

Journal of the American Chemical Society, 2012 , vol. 134, # 24 p. 9942 - 9945 Title/Abstract Full Text View citing articles Show Details

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, 1984 , vol. 32, # 9 p. 3345 - 3353 Title/Abstract Full Text Show Details

Multi-step reaction with 2 steps 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 View Scheme

Ohmori, Hidenobu; Furusako, Shoji; Kashu, Mieko; Ueda, Chihiro; Masui, Masaichiro

Chemical & Pharmaceutical Bulletin, 1984 , vol. 32, # 9 p. 3345 - 3353 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: C21H26N2; copper(I) bromide; sodium t-butanolate / cyclohexane / 48 h / 60 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 24 h / 40 °C View Scheme

Rx-ID: 33530902 Find similar reactions

Gildner, Peter G.; Gietter, Amber A. S.; Cui, Di; Watson, Donald A.

Journal of the American Chemical Society, 2012 , vol. 134, # 24 p. 9942 - 9945 Title/Abstract Full Text View citing articles Show Details

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Stage #1: With diphenyl phosphoryl azide; triethylamine in toluene

5 h; RefluxCooling; Stage #2: With hydrogenchloride; acetic acid in water

T=20°C; Hide Experimental Procedure

Rx-ID: 29555741 Find similar reactions

GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; BLACKLEDGE, Charles, William; BRADY, Gerald, Patrick; FENG, Yanhoug, G.; GRANT, Seth, W.; MEDINA, Jesus, Rahul; MILLER, William, H.; ROMERIL, Stuart, P.

Patent: WO2010/59658 A1, 2010 ; Location in patent: Page/Page column 158 ; Title/Abstract Full Text Show Details

75:

Intermediate 75; 2-Methyl-1 -phenyl-2-propanamine; DPPA (16.87 g, 61.31 mmol) was added with external cooling to a stirred solution of 2,2- dimethyl-3-phenylpropanoic acid (10.21 g, 57.30 mmol) and triethylamine (6.20 g, 61.3 mmol) in dry toluene (100 ml_). A slightly exothermic reaction commenced and was completed after about 1 hour. The reaction mixture was stirred for an additional 1 hour at room temperature, followed by refluxing for 3 hours. The solution was cooled and washed with water (3 X 100 ml_), and the toluene phase was separated, dried over Na2SO4, and evaporated in vacuum. A mixture of 15percent hydrochloric acid (20 ml.) and acetic acid (20 ml.) was added, and the resulting mixture was stirred at room temperature overnight. The mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (4 X 50 ml_), and the aqueous was concentrated in vacuum to afford the HCI salt of the title compound (5.21 g) as a white solid. LC-MS (ES) m/z = 150 [M+H]+. Stage #1: With diphenylphosphoranyl azide; triethylamine in toluene

T=20°C; Reflux; Stage #2: With hydrogenchloride; water; acetic acid

T=20°C; Hide Experimental Procedure

GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; BRADY, Gerald, Patrick, Jr.; GALLAGHER, Timothy, Francis; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul

Patent: WO2010/120854 A1, 2010 ; Location in patent: Page/Page column 115 ; Title/Abstract Full Text Show Details

DPPA (16.87 g, 61.31 mmol) was added with external cooling to a stirred solution of 2,2- dimethyl-3-phenylpropanoic acid (10.21 g, 57.30 mmol) and triethylamine (6.20 g, 61.3 mmol) in dry toluene (100 ml_). A slightly exothermic reaction commenced and was completed after about 1 hour. The reaction mixture was stirred for an additional 1 hour at room temperature, followed by refluxing for 3 hours. The solution was cooled and washed with water (3 X 100 ml_), and the toluene phase was separated, dried over Na2SO4, and evaporated in vacuum. A mixture of 15percent hydrochloric acid (20 ml.) and acetic acid (20 ml.) was added, and the resulting mixture was stirred at room temperature overnight. The mixture was partitioned between EtOAc and water. The aqueous layer was extracted withEtOAc (4 X 50 ml_), and the aqueous was concentrated in vacuum to afford the HCI salt of the title compound (5.21 g) as a white solid. LC-MS (ES) m/z = 150 [M+H]+.

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With piperidine in N,N-dimethyl-formamide

T=25°C;

Rx-ID: 29701981 Find similar reactions

Ishibashi, Yoshitaka; Miyata, Kengo; Kitamura, Masato

European Journal of Organic Chemistry, 2010 , # 22 p. 4201 - 4204 Title/Abstract Full Text View citing articles Show Details

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With hydrogen; water-d2; palladium on activated charcoal; platinum on activated charcoal

T=180°C; 24 h;

Rx-ID: 27953475 Find similar reactions

Ito, Nobuhiro; Watahiki, Tsutomu; Maesawa, Tsuneaki; Maegawa, Tomohiro; Sajiki, Hironao

Synthesis, 2008 , # 9 art. no. F03608SS, p. 1467 - 1478 Title/Abstract Full Text View citing articles Show Details

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With trifluorormethanesulfonic acid; [(cyclopentadienyl)Ru(IV)(quinaldinate) (allyl)](hexafluorophosphate) in methanol

T=30°C; 0.5 h;

Rx-ID: 10246308 Find similar reactions

Tanaka, Shinji; Saburi, Hajime; Murase, Takanori; Yoshimura, Masahiro; Kitamura, Masato

Journal of Organic Chemistry, 2006 , vol. 71, # 12 p. 4682 - 4684 Title/Abstract Full Text View citing articles Show Details

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With hydrochlorid acid in 1,4-dioxane; diethyl ether

Rx-ID: 23770584 Find similar reactions

Patent: US2006/69110 A1, 2006 ; Location in patent: Page/Page column 16 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

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With hydrogenchloride in tetrahydrofuran; water

T=20°C; 168 h;

Rx-ID: 8690702 Find similar reactions

Gajda; Koziara; Napieraj; Sikora; Zwierzak

Polish Journal of Chemistry, 2000 , vol. 74, # 10 p. 1385 - 1387 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 24295807 Find similar reactions

NPS Pharmaceuticals, Inc.; SmithKline Beecham, Corp.; SmithKline Beecham, PLC

Patent: US6022894 A1, 2000 ;

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Title/Abstract Full Text Show Details

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).

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Rx-ID: 6713021 Find similar reactions

Shetty

Journal of Organic Chemistry, 1961 , vol. 26, p. 3002 Full Text View citing articles Show Details

Manufactures J.R.Bottu

Patent: FR1551268 , 1968 ; Chem.Abstr., 1970 , vol. 72, # 12418s Full Text Show Details

Marquardt; Edwards

The Journal of organic chemistry, 1972 , vol. 37, # 11 p. 1861 - 1863 Title/Abstract Full Text View citing articles Show Details

Christol et al.

Bulletin de la Societe Chimique de France, 1961 , p. 2317 Full Text Show Details

Wallace and Tiesnan

Patent: GB910789 , 1963 ; Chem.Abstr., 1963 , vol. 59, # 2712 Full Text Show Details

University of Florida

Patent: US4771059 A1, 1988 ;

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Title/Abstract Full Text Show Details

STR61 TRANYLCYPROMINE ANILERIDINE PHENTERMINE

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Rx-ID: 2653804 Find similar reactions

With hydrogenchloride; triethyl phosphite in dichloromethane

1.) room temp., overnight, 2.) room temp., overnight; Yield given;

Koziara, Anna; Osowska-Pacewicka, Krystyna; Zawadzki, Stefan; Zwierzak, Andrzej

Synthesis, 1987 , # 5 p. 487 - 489 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: SnCl4, trimethylsilyl azide / CH2Cl2 / 144 h / 15 - 20 °C 2: 1.) triethyl phosphite, 2.) gas HCl / CH2Cl2 / 1.) room temp., overnight, 2.) room temp., overnight View Scheme

Rx-ID: 20385537 Find similar reactions

Koziara, Anna; Osowska-Pacewicka, Krystyna; Zawadzki, Stefan; Zwierzak, Andrzej

Synthesis, 1987 , # 5 p. 487 - 489 Title/Abstract Full Text Show Details

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With hydrogenchloride; hydrogen; palladium on activated charcoal in ethanol

T=50°C; P=760 Torr; Yield given;

Rx-ID: 3579782 Find similar reactions

Baldwin, Jack E.; Adlington, Robert M.; Newington, Ian M.

Journal of the Chemical Society, Chemical Communications, 1986 , # 2 p. 176 - 178 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: 100 percent 2: trifluoroacetic acid / 25 °C 3: conc. aq. HCl, H2 / 10percent Pd/C / ethanol / 50 °C / 760 Torr View Scheme

Rx-ID: 19033247 Find similar reactions

Baldwin, Jack E.; Adlington, Robert M.; Newington, Ian M.

Journal of the Chemical Society, Chemical Communications, 1986 , # 2 p. 176 - 178 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: trifluoroacetic acid / 25 °C 2: conc. aq. HCl, H2 / 10percent Pd/C / ethanol / 50 °C / 760 Torr View Scheme

Rx-ID: 19052010 Find similar reactions

Baldwin, Jack E.; Adlington, Robert M.; Newington, Ian M.

Journal of the Chemical Society, Chemical Communications, 1986 , # 2 p. 176 - 178 Title/Abstract Full Text View citing articles Show Details

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With hydrogenchloride; phosphoric acid; sodium nitrite

1.) MeOH, 3 h, reflux, water; Yield given. Multistep reaction;

Rx-ID: 2324675 Find similar reactions

Leclerc; Decker; Schwartz

Arzneimittel-Forschung/Drug Research, 1985 , vol. 35, # 9 p. 1357 - 1367 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2588815 Find similar reactions

Buchowiecki, Wieslaw; Grosman-Zjawiona, Zofia; Zjawiony, Jordan

Tetrahedron Letters, 1985 , vol. 26, # 9 p. 1245 - 1248 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 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 View Scheme

Rx-ID: 19069256 Find similar reactions

Leclerc; Decker; Schwartz

Arzneimittel-Forschung/Drug Research, 1985 , vol. 35, # 9 p. 1357 - 1367 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 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 View Scheme

Rx-ID: 19077499 Find similar reactions

Leclerc; Decker; Schwartz

Arzneimittel-Forschung/Drug Research, 1985 , vol. 35, # 9 p. 1357 - 1367 Title/Abstract Full Text View citing articles Show Details

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With citrate buffer; potassium chloride in ethanol

T=30°C; cotrolled potential electrolysis, cathod: Hg, vs. SCE;

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Rx-ID: 2102442 Find similar reactions

Ohmori, Hidenobu; Furusako, Shoji; Kashu, Mieko; Ueda, Chihiro; Masui, Masaichiro

Chemical & Pharmaceutical Bulletin, 1984 , vol. 32, # 9 p. 3345 - 3353 Title/Abstract Full Text Show Details

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With hydrogenchloride; sodium hydroxide

1.220 gradC, 24h;; Multistep reaction;

Rx-ID: 2086323 Find similar reactions

Dube, Michael F.; Timberlake, Jack W.

Tetrahedron, 1980 , vol. 36, p. 1753 - 1756 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2427013 Find similar reactions

Dube, Michael F.; Timberlake, Jack W.

Tetrahedron, 1980 , vol. 36, p. 1753 - 1756 Title/Abstract Full Text View citing articles Show Details

by neutralization;

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Synthesize Find similar Rx-ID: 3491655 Find similar reactions

T=37°C; metabolism;

Dell; Donik; Jacobi; Kamp

Arzneimittel-Forschung/Drug Research, 1980 , vol. 30, # 7 p. 1138 - 1144 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 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; View Scheme

Rx-ID: 20827683 Find similar reactions

Dube, Michael F.; Timberlake, Jack W.

Tetrahedron, 1980 , vol. 36, p. 1753 - 1756 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 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; View Scheme

Rx-ID: 20861292 Find similar reactions

Dube, Michael F.; Timberlake, Jack W.

Tetrahedron, 1980 , vol. 36, p. 1753 - 1756 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 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 View Scheme

Rx-ID: 20861294 Find similar reactions

Dube, Michael F.; Timberlake, Jack W.

Tetrahedron, 1980 , vol. 36, p. 1753 - 1756 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 25282303 Find similar reactions

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With KBH4 in methanol

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Warner-Lambert Company

Patent: US4018825 A1, 1977 ;

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Title/Abstract Full Text Show Details

13:Methyl 3-benzyloxy-5-[(2-(1,1 dimethyl-2-phenylethylamino)1-hydroxyethyl]-benzoate.

EXAMPLE 13 Methyl 3-benzyloxy-5-[(2-(1,1 dimethyl-2-phenylethylamino)1-hydroxyethyl]-benzoate. The 3-benzyloxy-5-carboxyphenylglyoxal (120 mmoles) was dissolved in MeOH (1 l.) and cooled to 0°. 1,1,-Dimethyl-2-phenyl-ethylamine (100 g, 0.67 moles) was added at 0° and the resulting mixture was stirred at 0° for 1 hr. before addition of KBH4 (12.2 g, 228 mmoles) over a period of 2 hrs. portionwise. The resultant mixture was allowed to react at room temperature for 18 hours before it was evaporated to a residual glass. The residue was acidified with 6N HCl (l l.) and extracted with CHCl3 (1 l.). Addition of ether to the CHCl3 extract gave the 1,1-dimethyl-2-phenylethylamine HCl as a white precipitate which was removed by filtration.

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Rx-ID: 377468 Find similar reactions

With sodium hydroxide

Ritter; Kalish

Journal of the American Chemical Society, 1948 , vol. 70, p. 4048 Organic Syntheses, 1964 , vol. 44, p. 44,45 Full Text View citing articles Show Details

With hydrogenchloride

Moed et al.

Recueil des Travaux Chimiques des Pays-Bas, 1955 , vol. 74, p. 919,922 Full Text Show Details

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With hypodiphosphonic acid; sodium nitrite

Rx-ID: 387090 Find similar reactions

Hass; Bender

Journal of the American Chemical Society, 1949 , vol. 71, p. 3482,3485 Full Text Show Details

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With hypodiphosphonic acid; sodium nitrite

Rx-ID: 455243 Find similar reactions

Kornblum; Iffland

Journal of the American Chemical Society, 1949 , vol. 71, p. 2137,2138,2140 Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: Raney nickel; ethanol / 60 °C / 58840.6 Torr / Hydrogenation 2: aqueous hypophosphoric acid; sodium nitrite View Scheme

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Rx-ID: 22082478 Find similar reactions

Hass; Bender

Journal of the American Chemical Society, 1949 , vol. 71, p. 3482,3485 Full Text Show Details

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Rx-ID: 22106218 Find similar reactions

Multi-step reaction with 3 steps 1: sodium ethylate solution 2: Raney nickel; ethanol / 60 °C / 58840.6 Torr / Hydrogenation 3: aqueous hypophosphoric acid; sodium nitrite View Scheme

Hass; Bender

Journal of the American Chemical Society, 1949 , vol. 71, p. 3482,3485 Full Text Show Details

Multi-step reaction with 3 steps 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 View Scheme

Hass; Bender

Journal of the American Chemical Society, 1949 , vol. 71, p. 3482,3485 Full Text Show Details

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With phosphorus; hydrogen iodide

Rx-ID: 393643 Find similar reactions

Zenitz; Macks; Moore

Journal of the American Chemical Society, 1948 , vol. 70, p. 955 Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid 2: aq. NaOH solution View Scheme

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Rx-ID: 22034758 Find similar reactions

Ritter; Kalish

Journal of the American Chemical Society, 1948 , vol. 70, p. 4048 Organic Syntheses, 1964 , vol. 44, p. 44,45 Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid 2: aq. NaOH solution View Scheme

Rx-ID: 22036057 Find similar reactions

Ritter; Kalish

Journal of the American Chemical Society, 1948 , vol. 70, p. 4048 Organic Syntheses, 1964 , vol. 44, p. 44,45 Full Text View citing articles Show Details

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Rx-ID: 6713022 Find similar reactions

With thionyl chloride

beim Hydrieren des erhaltenen (+-)-2-Chlor-1.1-dimethyl-2-phenylaethylamin-hydrochlorids an Palladium in Aethanol;

Merrell Co.

Patent: US2408345 , 1942 ; Full Text Show Details

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With calcium hydroxide powder; water

T=230°C;

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Rx-ID: 327876 Find similar reactions

Mentzer

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1941 , vol. 213, p. 581,583 Full Text Show Details

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Multi-step reaction with 2 steps 1: diethyl ether 2: calcium hydroxide; water / 230 °C View Scheme

Rx-ID: 22047352 Find similar reactions

Mentzer

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1941 , vol. 213, p. 581,583 Full Text Show Details

Synthesize Find similar

Rx-ID: 22053335 Find similar reactions

Multi-step reaction with 2 steps 1: aqueous potassium hypobromite 2: calcium hydroxide; water / 230 °C View Scheme

Mentzer

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1941 , vol. 213, p. 581,583 Full Text Show Details

Multi-step reaction with 3 steps 1: aqueous potassium hypobromite 2: diethyl ether 3: calcium hydroxide; water / 230 °C View Scheme

Mentzer

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1941 , vol. 213, p. 581,583 Full Text Show Details