N-Methyl-1-phenylpropan-2-amine (Methamphetamine) by Asch

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Reactions (34)

Yield

Substances (26)

Citations (24)

Conditions

References

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Rx-ID: 44430033 Find similar reactions

96 mg

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Stage #1: T=100°C; 2 h; Stage #2: With lithium aluminium tetrahydride in diethyl ether

5 h; Reflux; Hide Experimental Procedure

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CHIRON AS; Johansen, Jon Eigill; Liu, Huiling; Karlsen, Morten

Patent: US9435816 B2, 2016 ; Location in patent: Paragraph 15; 16 ; Title/Abstract Full Text Show Details

2:The Synthesis of DE-[’3C5]-Methamphetamine andIts Chloride Salt

Amphetamine free base (100 mg, 0.71 mmol) was dissolved in ethyl formate (10 mE). The solution was heated under pressure in an ACE pressure reactor for 2 hours at 100° C. The reaction mixture was cooled down, and the solvent was evaporated under reduced pressure. The resulting carbamate derivative was dissolved in dried diethyl ether (5 mE). The solution was added dropwise to a suspension of lithium aluminium hydride (40.4 mg, 1.07 mmol) in diethylether (10 mE). The reaction mixture was refluxed for 5hours. Thereafter, water was carefully added after the reaction mixture had been cooled down to 0° C. on an ice bath. The lithium salt was filtered over CeliteTM diatomaceous earth in l3uchner thnnel. The granules obtained were washed thoroughly with excess diethyl ethet The combined etherphases were washed with 5percent sodium hydroxide and brine before being dried with magnesium sulfate. The solvent was evaporated to yield 96 mg methamphetamine free base.The free base was redissolved in diethyl ethet The solution was cooled down to 10° C. before HC1 dissolves inisopropanol (1.85 mE) was added in small portions onto the pH reached 4. The resulting chloride salt was filtered off with a l3uchner funnel, washed with diethyl ether and dried to yield to 110 mg of the product with a purity >98.8percent as determined by TFAA. derivatization on GC-MS.

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Rx-ID: 4335062 Find similar reactions

Acs, Maria; Kozma, David; Fogassy, Elemer

ACH - Models in Chemistry, 1995 , vol. 132, # 3 p. 475 - 478 Title/Abstract Full Text Show Details

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Rx-ID: 4335063 Find similar reactions

Acs, Maria; Kozma, David; Fogassy, Elemer

ACH - Models in Chemistry, 1995 , vol. 132, # 3 p. 475 - 478 Title/Abstract Full Text Show Details

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With naphthalene; water-d2; lithium in tetrahydrofuran

1.) -78 deg C, 6 h, 2.) -78 - 20 deg C, 3 h;

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Rx-ID: 3822018 Find similar reactions

Almena, Juan; Foubelo, Francisco; Yus, Miguel

Journal of Organic Chemistry, 1994 , vol. 59, # 11 p. 3210 - 3215 Title/Abstract Full Text View citing articles Show Details

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With naphthalene; water-d2; lithium in tetrahydrofuran

1.) -78 deg C, 6 h, 2.) -78 - 20 deg C, 3 h;

Rx-ID: 3822029 Find similar reactions

Almena, Juan; Foubelo, Francisco; Yus, Miguel

Journal of Organic Chemistry, 1994 , vol. 59, # 11 p. 3210 - 3215 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2950897 Find similar reactions

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Zappey, Herman; Fokkens, Roel H.; Ingemann, Steen; Nibbering, Nico M. M.; Florencio, Helena

Organic Mass Spectrometry, 1991 , vol. 26, # 6 p. 587 - 594 Title/Abstract Full Text Show Details

ΔHΓ0; Thermodynamic data;

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Rx-ID: 2950902 Find similar reactions

ΔHΓ0; Thermodynamic data;

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Zappey, Herman; Fokkens, Roel H.; Ingemann, Steen; Nibbering, Nico M. M.; Florencio, Helena

Organic Mass Spectrometry, 1991 , vol. 26, # 6 p. 587 - 594 Title/Abstract Full Text Show Details

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Rx-ID: 2950906 Find similar reactions

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Zappey, Herman; Fokkens, Roel H.; Ingemann, Steen; Nibbering, Nico M. M.; Florencio, Helena

Organic Mass Spectrometry, 1991 , vol. 26, # 6 p. 587 - 594 Title/Abstract Full Text Show Details

ΔHΓ0; Thermodynamic data;

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Rx-ID: 24800469 Find similar reactions

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DR PHARMA NOVA, LLC

Patent: WO2006/91885 A2, 2006 ; Location in patent: Page/Page column 49-50 ;

Stage #1: in benzene

2 h; Heating / reflux; Stage #2: With lithium aluminium tetrahydride in diethyl ether

T=20°C; 1 h; Hide Experimental Procedure

Title/Abstract Full Text Show Details

27:

The amphetamine a-9 (10 mmol) is combined with 3.33 mmol para-formaldehyde in 50 mL dry benzene. The mixture is placed in a round bottom flask affixed with a Dean-Stark trap. The EPO <DP n="51"/>mixture is refluxed for two hours with continuous removal of water. The benzene is then removed using reduced pressure. To the residue is added 50 mL dry Et2ψ and an excess of LiAlEU is slowly added. The mixture is stirred for one hour at room temperature. The reaction is quenched slowly with water, and extracted with CH2CI2. The organic layer is dried using anhydrous MgSψ4 and evaporated to produce labeled mefhamphetaniine a-19. See Bartroli and co-workers, J. Med. Chem. (1998), 41, 1855-1868; Konosu and coworkers, Chem. Pharm. Bull. (1991), 39, 2581-2589. A

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With lithium aluminium tetrahydride

Title compound not separated from byproducts;

Harris, Debra S.; Boxenbaum, Harold; Everhart, E. Thomas; Sequeira, Gina; Mendelson, John E.; Jones, Reese T.

Clinical Pharmacology and Therapeutics, 2003 , vol. 74, # 5 p. 475 - 486 Title/Abstract Full Text View citing articles Show Details

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Stage #1: With lithium aluminium deuteride in tetrahydrofuran

Reflux; Stage #2: With sodium hydroxide in tetrahydrofuran; water

T=0 - 20°C; Hide Experimental Procedure

Rx-ID: 29946439 Find similar reactions

AUSPEX PHARMACEUTICALS, INC.

Patent: US2010/286124 A1, 2010 ; Location in patent: Page/Page column 11 ; Title/Abstract Full Text Show Details

1.3:

(R)-N-d3-Methyl-1-phenylpropan-2-amine: A solution of (R)-(1-methyl-2-phenyl-ethyl)-carbamic acid t-butyl ester (1.17 g, 4.98 mmol) in anhydrous tetrahydrofuran (5 mL) was added dropwise to a suspension of lithium aluminum deuteride in anhydrous tetrahydrofuran (30 mL). The resulting mixture was heated at reflux for about 2 hours and then was cooled to 0-5° C. Water (2 mL) and 2N sodium hydroxide (2 mL) were added sequentially. The resulting mixture was stirred at ambient temperature for about 16 hours and then filtered. The filtrate was washed with ethyl acetate, the ethyl acetate layers were combined, dried, and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (dichloromethane/methane/aqueous ammonia (10:1:0.1)) to give the title compound as a colorless oil (0.65 g; yield=86percent). 1H-NMR (CDCl3): δ1.05 (d, J=6.9 Hz, 3H), 1.40 (br s, 1H), 2.61 (m, 1H), 2.70 (m, 1H), 2.78 (m, 1H), 7.10-7.32 (m, 5H). MS: m/z 153.3 (M++1).

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Stage #1: With tritium; 20 palladium hydroxide on carbon; triethylamine in tetrahydrofuran; methanol

P=650 Torr; Stage #2: in methanol

pH=11.2; aq. phosphate buffer;

Rx-ID: 29475642 Find similar reactions

Lamb, Pamela B.; McElhinny, Charles J.; Sninski, Todd; Purdom, Hunter; Carroll, F. Ivy; Lewin, Anita H.

Journal of Labelled Compounds and Radiopharmaceuticals, 2009 , vol. 52, # 11 p. 457 - 462 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 7899377 Find similar reactions

Fentiman; Foltz

Journal of Labelled Compounds and Radiopharmaceuticals, 1976 , vol. 12, p. 69,74 Full Text Show Details

aus entspr. N-Carbethoxyverbdg., LiAlD4 <Δ>;

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Rx-ID: 25122927 Find similar reactions

Farmitalia Carlo Erba S.p.A.

Patent: US4444773 A1, 1984 ;

in PPA

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Title/Abstract Full Text Show Details

EXAMPLE 1 2-amino-thiazole (3.06 g) was reacted with ethyl 2-methylacetoacetate (6.4 g) in polyphosphoric acid (15.3 g:

EXAMPLE 1 2-amino-thiazole (3.06 g) was reacted with ethyl 2-methylacetoacetate (6.4 g) in polyphosphoric acid (15.3 g: 7.1 g of P2 O5 and 8.2 g of 99percent H3 PO4) under stirring at 100° C. for two hours. After cooling, dilution with ice water and neutralization, the precipitate was filtered, washed with water and crystallized from isopropyl ether to give 6,7-dimethyl-5H-thiazolo[3,2-a]pyrimidine-5-one, m.p. 112°-113° C. (5.04 g), which was reacted with 3-pyridinecarboxaldehyde (5.99 g) in methanol (130 ml) in the presence of sodium methoxide (4.55 g) under stirring at reflux temperature for 12 hours.

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With phosphate buffer

T=105°C; ΔE(excit.); other reagent; other temperature; Thermodynamic dataRate constantKinetics;

Rx-ID: 3987254 Find similar reactions

Chafetz; Desai; Sukonik

Journal of Pharmaceutical Sciences, 1994 , vol. 83, # 9 p. 1250 - 1252 Title/Abstract Full Text View citing articles Show Details

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With palladium on barium sulfate in water

T=20°C; 4 h;

Rx-ID: 25930801 Find similar reactions

Matsumoto, Teruki; Urano, Yasuteru; Makino, Yukiko; Kikura-Hanajiri, Ruri; Kawahara, Nobuo; Goda, Yukihiro; Nagano, Tetsuo

Analytical Chemistry, 2008 , vol. 80, # 4 p. 1176 - 1181 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 25930802 Find similar reactions

With ammonia; lithium in tetrahydrofuran

T=-78°C; 0.0833333 h;

Matsumoto, Teruki; Urano, Yasuteru; Makino, Yukiko; Kikura-Hanajiri, Ruri; Kawahara, Nobuo; Goda, Yukihiro; Nagano, Tetsuo

Analytical Chemistry, 2008 , vol. 80, # 4 p. 1176 - 1181 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: hydrochlorid acid / methanol / 0.5 h / 760.05 Torr 2: palladium 10 on activated carbon; hydrogen / methanol / 16 h / 20 °C View Scheme

Lalwani, Komal G.; Sudalai, Arumugam

Tetrahedron Letters, 2015 , vol. 56, # 46 p. 6488 - 6490 Title/Abstract Full Text View citing articles Show Details

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Stage #1: With iodine; hypophosphorous acid

Heating; Stage #2: With sodium hydroxide in water

pH=> 10; Stage #3: With hydrogenchloride in toluene

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Rx-ID: 25930803 Find similar reactions

David, Gabrielle E.; Hibbert, D. Brynn; Frew, Russell D.; Hayman, Alan R.

Australian Journal of Chemistry, 2010 , vol. 63, # 1 p. 22 - 29 Title/Abstract Full Text View citing articles Show Details

65%

With phosphorus; hydrogen iodide

T=140°C; 4.5 h;

Matsumoto, Teruki; Urano, Yasuteru; Makino, Yukiko; Kikura-Hanajiri, Ruri; Kawahara, Nobuo; Goda, Yukihiro; Nagano, Tetsuo

Analytical Chemistry, 2008 , vol. 80, # 4 p. 1176 - 1181 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / water / 12 h / 20 °C 2: Raney Ni / isopropyl alcohol / 50 - 55 °C / |Autoclave 3: hydrogenchloride / ethyl acetate / 20 h / 0 - 20 °C / |Large scale View Scheme

Pramanik, Chinmoy; Bapat, Kiran; Chaudhari, Ashok; Kulkarni, Mukund G.; Kolla, Rangarao; Sompalli, Srinivasarao; Tripathy, Narendra K.; Gurjar, Mukund K.

Organic Process Research and Development, 2014 , vol. 18, # 4 p. 495 - 500 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 25930804 Find similar reactions

77%

With palladium 10 on activated carbon; hydrogen in methanol

T=20°C; 16 h; enantioselective reaction; Show Experimental Procedure

Lalwani, Komal G.; Sudalai, Arumugam

Tetrahedron Letters, 2015 , vol. 56, # 46 p. 6488 - 6490 Title/Abstract Full Text View citing articles Show Details

65%

With hydrochlorid acid; phosphorus

T=140°C; 4.5 h;

Matsumoto, Teruki; Urano, Yasuteru; Makino, Yukiko; Kikura-Hanajiri, Ruri; Kawahara, Nobuo; Goda, Yukihiro; Nagano, Tetsuo

Analytical Chemistry, 2008 , vol. 80, # 4 p. 1176 - 1181 Title/Abstract Full Text View citing articles Show Details

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With hydrogenchloride in toluene

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Rx-ID: 29189894 Find similar reactions

Kunalan, Vanitha; Daeid, Niamh Nic; Kerr, William J.; Buchanan, Hilary A. S.; McPherson, Allan R.

Analytical Chemistry, 2009 , vol. 81, # 17 p. 7342 - 7348 Title/Abstract Full Text View citing articles Show Details

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Stage #1: With iodine; hypophosphorous acid

Heating; Stage #2: With sodium hydroxide in water

pH=> 10; Stage #3: With hydrogenchloride in toluene

Rx-ID: 29344283 Find similar reactions

David, Gabrielle E.; Hibbert, D. Brynn; Frew, Russell D.; Hayman, Alan R.

Australian Journal of Chemistry, 2010 , vol. 63, # 1 p. 22 - 29 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: Raney Ni / isopropyl alcohol / 50 - 55 °C / |Autoclave 2: hydrogenchloride / ethyl acetate / 20 h / 0 - 20 °C / |Large scale View Scheme

Rx-ID: 37769150 Find similar reactions

Pramanik, Chinmoy; Bapat, Kiran; Chaudhari, Ashok; Kulkarni, Mukund G.; Kolla, Rangarao; Sompalli, Srinivasarao; Tripathy, Narendra K.; Gurjar, Mukund K.

Organic Process Research and Development, 2014 , vol. 18, # 4 p. 495 - 500 Title/Abstract Full Text View citing articles Show Details

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T=0 - 20°C; 20 h; Large scale;

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Rx-ID: 37769156 Find similar reactions

Pramanik, Chinmoy; Bapat, Kiran; Chaudhari, Ashok; Kulkarni, Mukund G.; Kolla, Rangarao; Sompalli, Srinivasarao; Tripathy, Narendra K.; Gurjar, Mukund K.

Organic Process Research and Development, 2014 , vol. 18, # 4 p. 495 - 500 Title/Abstract Full Text View citing articles Show Details

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Stage #1: With phosphorus; water-d2

Heating; Stage #2: With sodium hydroxide in water

pH=> 10; Stage #3: With hydrogenchloride in toluene

Rx-ID: 29344284 Find similar reactions

David, Gabrielle E.; Hibbert, D. Brynn; Frew, Russell D.; Hayman, Alan R.

Australian Journal of Chemistry, 2010 , vol. 63, # 1 p. 22 - 29 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 38014750 Find similar reactions

81%

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Stage #1: T=100°C; 2 h; Autoclave; Stage #2: With lithium aluminium tetrahydride in diethyl ether

5 h; Reflux; Stage #3: With hydrogenchloride in diethyl ether; isopropyl alcohol

pH=4;

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Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge

Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details

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With hydrogenchloride in diethyl ether; isopropyl alcohol

T=10°C; pH=4; Hide Experimental Procedure

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Rx-ID: 44430044 Find similar reactions

CHIRON AS; Johansen, Jon Eigill; Liu, Huiling; Karlsen, Morten

Patent: US9435816 B2, 2016 ; Location in patent: Page/Page column 15; 16 ; Title/Abstract Full Text Show Details

2:The Synthesis of DE-[’3C5]-Methamphetamine andIts Chloride Salt

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Rx-ID: 29591318 Find similar reactions

4.65 g

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Schulze, Matthias

Synthetic Communications, 2010 , vol. 40, # 10 p. 1461 - 1476 Title/Abstract Full Text View citing articles Show Details

in ethanol

0.5 h;

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Rx-ID: 23831711 Find similar reactions

B: 98.8%

T=100 - 145°C; 3.38333 h; Product distribution / selectivity; Hide Experimental Procedure

MALLINCKRODT INC.

Patent: WO2006/73547 A1, 2006 ; Location in patent: Page/Page column 6-7 ; Title/Abstract Full Text Show Details

EXAMPLE 1.; 0025] To a 150 ml 3-neck flask fitted with a mechanical stirrer, a condenser and an addition funnel was added 23.12 g (0.1549 mole) of methamphetamine base. A nitrogen purge was started and maintained throughout the reaction to prevent the formation of colored byproducts. The methamphetamine was stirred and heated to 100° C. Then 9.79 g (0.0773 mole) of benzyl chloride was added drop wise over a period of 23 minutes. Heat of reaction raised the temperature of the reaction mixture to 145° C. The reaction appeared to be instantaneous as the benzyl chloride was introduced. After the addition of the benzyl chloride was completed the reaction mass temperature dropped and heat was supplied to maintain a temperature of the reaction mass at 120° C for a total of three hours. No foaming was observed. During the reaction methamphetamine hydrochloride precipitated out of the solution. As the mixture thickened a 15.74 g portion of toluene was added to aid mixing. After three hours the mixture was cooled to ambient temperature and vacuum filtered providing 13.48 g (98.8percent yield after adjusting for samples taken during the reaction) on a dry basis of white methamphetamine hydrochloride crystals having a melting point of 172.4- 178.4° C (lit. 170-175° C). An HPLC analysis found 92.5 area percent methamphetamine and 3.8 areapercent benzphetamine. The product, benzphetamine base was in the filtrate and completely separated from the methamphetamine hydrochloride.[0026] The separated benzphetamine base (68.70 g) in a toluene solution was converted to the hydrochloride salt by addition of 7.80 g of concentrated hydrochloric acid (37.5percent). The salt was transferred to a separatory funnel and the 3-neck flask was rinsed with 16.60 g of water. The layers were separated into a 41.55 g water layer containing the benzphetamine hydrochloride and a 49.23 g toluene layer, which would contain any unreacted benzyl chloride.[0027] The water layer containing the benzphetamine hydrochloride was transferred to a 300 ml 3-neck flask fitted with a mechanical stirrer and a Dean-Stark trap and condenser. The EPO <DP n="8"/>separatory funnel was then rinsed with 6.54 g of water. Then 190.1 g of toluene was added and the water was removed by azeotropic distillation. After water removal, the toluene was distilled forward until there was a total of 196.98 g of water/toluene distillate collected. Fresh toluene, 59 g, was then added to the 300 ml flask. The mixture was stirred and 46.49 g of toluene was distilled from the flask. The remaining mixture in the flask was cooled to ambient temperature, then slowly heated, whereupon rapid crystallization occurred. The mixture was then cooled to less than 10° C to maximize product recovery. Vacuum filtration provided 20.77 g of benzphetamine hydrochloride wet cake and 42.41 g of filtrate. The wet cake was dried in a vacuum oven at 60° C for 1.5 hours providing 18.59 g (89.4percent yield after adjusting for samples taken) of white benzphetamine hydrochloride crystals having a melting point of 147.0-152.1° C. HPLC analysis found 94.9 areapercent benzphetamine and 4.3 areapercent methamphetamine. Such yield represents an improvement over the prior art procedure employing sodium carbonate to neutralize the HCl in the reaction mixture, which typically provided a yield of about 70percent. A

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Rx-ID: 23831710 Find similar reactions

B: 95%

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MALLINCKRODT INC.

Patent: WO2006/73547 A1, 2006 ; Location in patent: Page/Page column 7-8 ;

in water; toluene

T=70 - 120°C; 8.16667 h; Product distribution / selectivity; Hide Experimental Procedure

Title/Abstract Full Text Show Details

EXAMPLE 2.; [0029] To a 100 ml 3 -neck flask fitted with a mechanical stirrer, a condenser and an addition funnel was added 24.11 g (0.1615 mole) of methamphetamine base and 9.64 g of toluene. A nitrogen purge was started and maintained throughout the reaction to prevent the formation of colored by-products. The methamphetamine solution was stirred and heated to 120° C. Then 10.74 g (0.0848 mole) of benzyl chloride was added drop wise over a period of 40 minutes. After the addition of the benzyl chloride was completed the reaction mass temperature was maintained at 120° C for a total of seven hours. No foaming was observed. During the reaction methamphetamine hydrochloride precipitated out of the solution. After seven hours the reaction mixture was cooled to about 70° C and then 27.65 g of additional toluene and 50.84 g of water was added. The mixture was stirred and heated to 70 ° C for 30 minutes. Then the mixture was cooled to ambient temperature and the two liquid layers were separated into a 65.28 g lower water layer containing the methamphetamine hydrochloride and a 51.47 g upper organic layer containing the benzphetamine base. An HPLC analysis found 99.8 percent of the methamphetamine partitioned to the water layer and 100percent of the benzphetamine partitioned to the organic layer. The product, benzphetamine base was nearly completely separated from the methamphetamine hydrochloride. The yield of benzphetamine hydrochloride was 95percent of the theoretical amount. EPO <DP n="9"/>)030] Similar results were obtained for the benzylation of propylhexedrine by the reaction of a benzylhalide with propylhexedrine wherein a molar excess of propylhexedrine, in the range of about 2 to 1 with respect to the benzylhalide, is employed. A

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Rx-ID: 1553378 Find similar reactions

Fogassy, Elemer; Acs, Maria; Faigl, Ferenc; Simon, Kalman; Rohonczy, Janos; Ecsery, Zoltan

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986 , p. 1881 - 1886 Title/Abstract Full Text View citing articles Show Details

in ethanol

T=5°C; 72 h;

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Find similar Rx-ID: 4415692 Find similar reactions

90%

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With hydrogenchloride in water

T=80°C;

Crock, Piero Dalla; Ferraccioli, Raffaella; Rosa, Concetta L.A.

Gazzetta Chimica Italiana, 1996 , vol. 126, # 2 p. 107 - 109 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 8365484 Find similar reactions

Laboratoire d'Analyses et de Recherches Biologiques Mauvernay; C.E.R.M.

Patent: BE639286 , 1962 ; Chem.Abstr., 1965 , vol. 62, # 11738b Full Text Show Details

aus entspr. Komponenten;

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B: 87%

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Rx-ID: 25425347 Find similar reactions

Schering Corporation

Patent: US3956390 A1, 1976 ; Title/Abstract Full Text Show Details

3:Desulfonylation of N-mesyldesoxyephedrine

EXAMPLE 3 Desulfonylation of N-mesyldesoxyephedrine The procedure of Example 2 is repeated except that 9.66 grams of D-N-mesyldesoxyephedrine (0.0425 mole) is substituted for the tosyl analog. The reflux time is reduced to 4 hours. After addition of the picric acid, an 87percent yield of D-desoxyephedrine picrate is recovered.

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Rx-ID: 35628789 Find similar reactions

With hydrogenchloride in water

336 - 672 h;

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Wood, Matthew R.; Lalancette, Roger A.

Acta Crystallographica Section C: Crystal Structure Communications, 2013 , vol. 69, # 4 p. 388 - 393 Title/Abstract Full Text View citing articles Show Details