(S)-N-Methyl-1-phenylpropan-2-amine [(S)-(+)-Methamphetamine] by Asch

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Reactions (55)

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Substances (2)

Citations (35)

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References

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With ammonia; lithium in tetrahydrofuran

T=-78 - -20°C; 1 h; Reagent/catalyst; Hide Experimental Procedure

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Rx-ID: 356231 Find similar reactions

Satara Pharmaceuticals, LLC; Rajagopalan, Raghavan

Patent: US2016/89439 A1, 2016 ; Location in patent: Paragraph 0044 ; Title/Abstract Full Text Show Details

1:Example 1 General Procedure for the Reaction of the Excipient of Formulas I and II and Pseudoephedrine with Lithium in Liquid Ammonia

General procedure: Example 1 General Procedure for the Reaction of the Excipient of Formulas I and II and Pseudoephedrine with Lithium in Liquid Ammonia (0044) Lithium metal pieces (35 mg, 5.0 mmol) were carefully added to liquid ammonia (5-10 mL) at about −78° C. (dry ice, isopropyl alcohol). A dark blue solution began to form within a few seconds. The dark blue solution was stirred at −78° C. for about 3 to 5 minutes. Thereafter, a mixture of the excipient of Formula I (122-166 mg, 1.0 mmol) and pseudoephedrine (165 mg, 1.0 mmol) in anhydrous tetrahydrofuran (3 mL) was added to the dark blue solution. The entire reaction mixture was stirred while the temperature of the reaction was slowly raised to about −20° C. Stirring was continued at this temperature for about 1 hour. The reaction mixture was quenched with saturated ammonium chloride (2 mL) and water (3 mL), and diluted with methanol (5 mL). The reaction mixture was analyzed and quantified for the presence of methamphetamine. The results are given in Example 3 below. 1%

With acetylpyrazine; ammonia; lithium in tetrahydrofuran

T=-78 - -20°C; 1 h; Reagent/catalystTemperatureTime; Hide Experimental Procedure

DAYA DRUG DISCOVERIES, INC.; RAJAGOPALAN, Raghavan

Patent: WO2015/48597 A1, 2015 ; Location in patent: Page/Page column 9-10 ; Title/Abstract Full Text Show Details

Example 1. General Procedure for the reaction of the exipient of Formulas I and II and pseudoephedrine with lithium in liquid ammonia. Lithium metal pieces (35 mg, 5.0 mmol) were carefully added to liquid ammonia (510 mL) at about -78 °C (dry ice, isopropyl alcohol). A dark blue solution began to form within a few seconds. The dark blue solution was stirred at -78 °C for about 3 to 5 minutes. Thereafter, a mixture of the exipient of Formula I (122-166 mg, 1.0 mmol) and pseudoephedrine (165 mg, 1 .0 mmol) in anhydrous tetrahydrofuran (3 mL) was added to the dark blue solution. The entire reaction mixture was stirred while the temperature of the reaction was slowly raised to about - 20 °C. Stirring was continued at this temperature for about 1 hour. The reaction mixture was quenched with saturated ammonium chloride (2 mL) and water (3 mL), and diluted with methanol (5 mL). The reaction mixture was analyzed and quantified for the presence of methamphetamine. The results are given in Example 3 below. With phosphorus; hydrogen iodide

Ogata; zit. bei Emde

Helvetica Chimica Acta, 1929 , vol. 12, p. 373 Full Text Show Details

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Multi-step reaction with 5 steps 1.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C / |Inert atmosphere 1.2: 0.08 h / -78 °C 1.3: 12 h / -78 - 25 °C 2.1: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / 0 - 25 °C 3.1: palladium 10 on activated carbon; hydrogen / methanol / 5 h / 25 °C / 760.05 Torr 4.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 25 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / |Reflux View Scheme

Rx-ID: 39182429 Find similar reactions

Dey, Soumen; Sudalai, Arumugam

Tetrahedron Asymmetry, 2015 , vol. 26, # 1 p. 67 - 72 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / 0 - 25 °C 2: palladium 10 on activated carbon; hydrogen / methanol / 5 h / 25 °C / 760.05 Torr 3: triethylamine; dmap / dichloromethane / 3 h / 0 - 25 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / |Reflux View Scheme

Rx-ID: 39182435 Find similar reactions

Dey, Soumen; Sudalai, Arumugam

Tetrahedron Asymmetry, 2015 , vol. 26, # 1 p. 67 - 72 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 3 h / 0 - 25 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / |Reflux View Scheme

Rx-ID: 39182438 Find similar reactions

Dey, Soumen; Sudalai, Arumugam

Tetrahedron Asymmetry, 2015 , vol. 26, # 1 p. 67 - 72 Title/Abstract Full Text View citing articles Show Details

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With lithium aluminium tetrahydride in tetrahydrofuran

4 h; Reflux; Hide Experimental Procedure

Rx-ID: 39182442 Find similar reactions

Dey, Soumen; Sudalai, Arumugam

Tetrahedron Asymmetry, 2015 , vol. 26, # 1 p. 67 - 72 Title/Abstract Full Text View citing articles Show Details

(R)-N-Methyl-1-phenylpropan-2-amine 11

General procedure: To a stirred solution of N-Boc protected amino alcohol 9 (0.5mg, 1.98mmol) in CH2Cl2 (5mL) were added dry triethylamine (0.3mL, 2.37mmol) and p-toluenesulfonyl chloride (0.452g, 2.37mmol) in the presence of a catalytic amount of 4-dimethylaminopyridine (0.024g,10molpercent) at 0°C. The reaction mixture was stirred at 25°C for 3h and then quenched by addition of 10percent NaHCO3. The aqueous layer was extracted with CH2Cl2 (3×20mL) and the combined organic layers were dried over anhydrous Na2SO4, and concentrated to give the crude tosylate, which was then dissolved in dry THF (5mL), and added dropwise to a suspension of LiAlH4 (0.225g, 3mmol) in dry THF (10mL). The mixture was refluxed for 4h and then cooled to 0°C after which the excess LiAlH4 was quenched by the addition of EtOAc. It was then treated with aq. 20percent NaOH (0.5mL). The white precipitate which formed was filtered off, and the residue was washed with EtOAc (3×10mL). The combined EtOAc layers were dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography over silica gel using CHCl3 as the eluent to afford the corresponding pure N-methyl amine 11. Yield: 0.192g, 65percent; [α]D25=–10.8 (c 4.2, EtOH); {lit.20 [α]D25=−10.9 (c 4.2, EtOH)}; IR (CHCl3, cm−1) 3274, 2917, 2839, 1614,1438; 1H NMR (200MHz, CDCl3): δ 7.15–7.28 (m, 5H), 2.63–2.82 (m, 3H), 2.4 (s, 3H), 1.67 (br s, 1H), 1.08 (d, J=5.9Hz, 3H); 13C NMR (50MHz, CDCl3): δ 139.2, 129.2, 128.4, 126.2, 56.3, 43.3, 33.8, 13.6; Anal. Calcd for C10H15N requires C 80.48; H 10.13; N 9.39percent; found C 80.50; H 10.11; N 9.35percent.

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Rx-ID: 39182454 Find similar reactions

Multi-step reaction with 3 steps 1: palladium 10 on activated carbon; hydrogen / methanol / 5 h / 25 °C / 760.05 Torr 2: triethylamine; dmap / dichloromethane / 3 h / 0 - 25 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / |Reflux View Scheme

Dey, Soumen; Sudalai, Arumugam

Tetrahedron Asymmetry, 2015 , vol. 26, # 1 p. 67 - 72 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 6 steps 1.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 4 h / -20 °C 1.2: 8.25 h / -20 - 25 °C 2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C / |Inert atmosphere 2.2: 0.08 h / -78 °C 2.3: 12 h / -78 - 25 °C 3.1: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / 0 - 25 °C 4.1: palladium 10 on activated carbon; hydrogen / methanol / 5 h / 25 °C / 760.05 Torr 5.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 25 °C 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / |Reflux View Scheme

Rx-ID: 39182508 Find similar reactions

Dey, Soumen; Sudalai, Arumugam

Tetrahedron Asymmetry, 2015 , vol. 26, # 1 p. 67 - 72 Title/Abstract Full Text View citing articles Show Details

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With (S)-N-isopropyl-N-methyl-2-ammonium-2'-bis(pentafluorophenyl)hydroborate1,1'-binaphthyl; hydrogen in tert-butyl methyl ether

T=25°C; P=1500.15 Torr; 16 h; Schlenk technique; Overall yield = 72 percent; Optical yield = 32 percent ee; enantioselective reaction;

Lindqvist, Markus; Borre, Katja; Axenov, Kirill; Kótai, Bianka; Nieger, Martin; Leskelä, Markku; Pápai, Imre; Repo, Timo

Journal of the American Chemical Society, 2015 , vol. 137, # 12 p. 4038 - 4041 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 40463175 Find similar reactions

CHEMAPOTHECA, LLC; Meckler, Harold; Gregg, Brian Thomas; Yang, Jie

Patent: US2015/183716 A1, 2015 ;

Multi-step reaction with 3 steps 1: copper(l) chloride / tetrahydrofuran / 0.5 h / 46 - 51 °C 2: potassium tert-butylate / tetrahydrofuran / 0.17 h / 20 °C 3: hydrogenchloride / water / 2.5 h / 80 °C View Scheme

Title/Abstract Full Text Show Details

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Rx-ID: 40463182 Find similar reactions

CHEMAPOTHECA, LLC; Meckler, Harold; Gregg, Brian Thomas; Yang, Jie

Patent: US2015/183716 A1, 2015 ;

Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 20 °C 2: hydrogenchloride / water / 2.5 h / 80 °C View Scheme

Title/Abstract Full Text Show Details

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75%

With hydrogenchloride in water

T=80°C; 2.5 h; Hide Experimental Procedure

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Rx-ID: 40463192 Find similar reactions

CHEMAPOTHECA, LLC; Meckler, Harold; Gregg, Brian Thomas; Yang, Jie

Patent: US2015/183716 A1, 2015 ; Location in patent: Paragraph 0155; 0158; 0159 ; Title/Abstract Full Text Show Details

Preparation of d-N-methylamphetamine (9) from 8

Preparation of d-N-methylamphetamine (9) from 8 A 50 mL, 3-necked round bottomed flask was charged with 8 (0.5 g, 1.75 mmol) and 3 M HCl (25 mL) and the stirred reaction mixture was heated to 80° C. for 2.5 hours and then cooled to room temperature.

The orange solution was extracted with isopropyl acetate (25 mL) and the organic extract layer was discarded. Sodium hydroxide solution (50percent solution, 10 mL) was slowly added to the remaining aqueous layer, keeping the internal temperature below 25° C. Methyl tert-butyl ether (20 mL) was added and the reaction mixture was agitated for 20 minutes then allowed to separate for 30 minutes. The aqueous layer was removed and the organic layer washed with water (10 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a light brown oil. This oil was distilled (bulb-to-bulb at 65-67° C. 0.6 mm Hg vacuum) to afford 9 as a colorless oil (0.19 g, 75percent yield). This distillate was converted to the known HCl salt for analysis, mp 172-175° C. Optical rotation c=1.00, water, 25.2° C., +16.3°. A

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Stage #1: With Perfil 100TM; (2R,3S)-(-)-di-O-benzoyl tartaric acid in methanol

Stage #2: With sodium hydroxide in dichloromethane

0.0833333 h; Title compound not separated from byproducts;

Kmecz, Ildiko; Simandi, Bela; Szekely, Edit; Fogassy, Elemer

Tetrahedron Asymmetry, 2004 , vol. 15, # 12 p. 1841 - 1845 Title/Abstract Full Text View citing articles Show Details

With Perfil 100TM; (2R,3S)-(-)-di-O-benzoyl tartaric acid in methanol

Title compound not separated from byproducts;

Kmecz, Ildiko; Simandi, Bela; Szekely, Edit; Fogassy, Elemer

Tetrahedron Asymmetry, 2004 , vol. 15, # 12 p. 1841 - 1845 Title/Abstract Full Text View citing articles Show Details

With column LiChrospher 100 RP-18e; sulfated β-cyclodextrin in methanol; water

T=20°C; Reagent/catalyst;

Taschwer, Magdalena; Seidl, Yvonne; Mohr, Stefan; Schmid, Martin G.

Chirality, 2014 , vol. 26, # 8 p. 411 - 418 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 22069695 Find similar reactions

Multi-step reaction with 2 steps 1: alcohol / Reduktion des Reaktionsprodukts mit Natrium und Alkohol 2: d(+)-tartaric acid View Scheme

Ogata

Yakugaku Zasshi, 1919 , # 451 p. 751 Chem.Abstr., 1920 , vol. 14, p. 745 Full Text Show Details

With glucose dehydrogenase; D-glucose; S-selective imine reductase from Streptomyces aurantiacus; NADPH in aq. buffer T=20°C; pH=9.8; 20 h; Enzymatic reaction; Reagent/catalyst; stereoselective reaction;

Huber, Tobias; Schneider, Lisa; Praeg, Andreas; Gerhardt, Stefan; Einsle, Oliver; Mueller, Michael

ChemCatChem, 2014 , vol. 6, # 8 p. 2248 - 2252 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 7362650 Find similar reactions

Repke et al.

Journal of Pharmaceutical Sciences, 1978 , vol. 67, p. 1167,1168 Full Text Show Details

BASF SE

Patent: US2012/123155 A1, 2012 ; Location in patent: Page/Page column 11 ;

Title/Abstract Full Text Show Details

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Stage #1: With 20 palladium hydroxide on carbon; hydrogen in methanol

Reduced pressure; Stage #2: With sodium hydroxide in dichloromethane; water

Rx-ID: 29475641 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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With recombinant human acetylcholinesterase

T=37°C; Kinetics;

Verheijen, Jeroen C.; Wiig, Kjesten A.; Du, Shoucheng; Connors, Stacie L.; Martin, Ashley N.; Ferreira, Jennifer P.; Slepnev, Vladimir I.; Kochendoerfer, Ulrike

Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 12 p. 3243 - 3246 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 588054 Find similar reactions

With sulfuric acid; palladium; acetic acid

T=80°C; Hydrogenation;

Rosenmund; Karg

Chemische Berichte, 1942 , vol. 75, p. 1850,1856 Full Text Show Details

Kindler; Hedemann; Schaerfe

Justus Liebigs Annalen der Chemie, 1948 , vol. 560, p. 215,219 Full Text Show Details

With perchloric acid; palladium; acetic acid

T=60°C; Hydrogenation;

Rosenmund; Karg

Chemische Berichte, 1942 , vol. 75, p. 1850,1856 Full Text Show Details

Kindler; Hedemann; Schaerfe

Justus Liebigs Annalen der Chemie, 1948 , vol. 560, p. 215,219 Full Text Show Details

With thionyl chloride; palladium on barium sulfate; hydrogen; sodium acetate

1.) CHCl3, reflux, 3 h, 2.) AcOH; Yield given. Multistep reaction;

Noggle, F. Taylor; DeRuiter, Jack; Clark, C. Randall

Analytical Chemistry, 1986 , vol. 58, # 8 p. 1643 - 1648 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: thionyl chloride / CHCl3

2: H2 / Pd/C / ethanol View Scheme

Armellin, Silvia; Brenna, Elisabetta; Frigoli, Samuele; Fronza, Giovanni; Fuganti, Claudio; Mussida, Daniele

Analytical Chemistry, 2006 , vol. 78, # 9 p. 3113 - 3117 Title/Abstract Full Text View citing articles Show Details

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With hydrogen; palladium on activated charcoal in ethanol

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Rx-ID: 11117696 Find similar reactions

Armellin, Silvia; Brenna, Elisabetta; Frigoli, Samuele; Fronza, Giovanni; Fuganti, Claudio; Mussida, Daniele

Analytical Chemistry, 2006 , vol. 78, # 9 p. 3113 - 3117 Title/Abstract Full Text View citing articles Show Details

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78%

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Stage #1: With hydrogenchloride in water

T=104 - 105°C; 10 h; Heating / reflux; Stage #2: With sodium hydroxide in water

Product distribution / selectivity; Hide Experimental Procedure

Rx-ID: 23850605 Find similar reactions

EMMELLEN BIOTECH PHARMACEUTICALS LIMITED

Patent: WO2006/67794 A1, 2006 ; Location in patent: Page/Page column 17 ; Title/Abstract Full Text Show Details

2.C:

In a three necked 500 ml. round bottom flask equipped with thermo controller, stirrer and condenser was charged with N-formyl desoxy ephedrine ( 35 grams, 0.197 mole) and 1 :1 aq. HCl (175 ml). The reaction mixture was refluxed (reaction temperature 104- 1050C) while stirring for 10 hours. Cooled the reaction mass to 400C and extracted with toluene to remove neutral impurities. Aqueous layer was basified with aq. Sodium hydroxide and extracted with diisopropyl ether (2 X 100 ml). The organic layers were washed with water and dried over sodium sulphate. Solvent was removed by distillation under vacuum, which afforded methamphetamine as a pale yellow to white clear liquid. (23 grams, 78 percent yield), Specific optical rotation.: + 17.3° (2percent solution in 1.2N HCl) ; purity: (GLC): 98.2percent].

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87.17%

Stage #1: With hydrogenchloride in water

T=104 - 105°C; 12 h; Heating / reflux; Stage #2: With sodium hydroxide in water

Product distribution / selectivity; Hide Experimental Procedure

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Rx-ID: 23850609 Find similar reactions

EMMELLEN BIOTECH PHARMACEUTICALS LIMITED

Patent: WO2006/67794 A1, 2006 ; Location in patent: Page/Page column 19 ; Title/Abstract Full Text Show Details

4.C:

In a three necked 500 ml. round bottom flask equipped with thermo controller, stirrer and condenser was charged with N-acetyl desoxy ephedrine (50 grams, 0.261 mole) and 1:1 aq. HCl (250 ml). The reaction mixture was refluxed (reaction temperature 104 - 1050C) while stirring for 12 hours. Cooled the reaction mass to 400C and extracted with toluene to remove neutral impurities. Aqueous layer was basified with aq. Sodium hydroxide and extracted with diisopropyl ether (2 X 200 ml). The organic layers were pooled and washed with water and dried over sodium sulphate. Solvent was removed by distillation under vacuum, which afforded methamphetamine as a pale yellow to white clear liquid. (34 grams, 87.17percent yield), Specific optical rotation.: +17.8° (2percent solution in 1.2N HCl); purity : (GLC: 99percent)

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71%

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Stage #1: With hydrogenchloride in water

T=104 - 105°C; 13 h; Heating / reflux; Stage #2: With sodium hydroxide in water

Product distribution / selectivity; Hide Experimental Procedure

Rx-ID: 23850614 Find similar reactions

EMMELLEN BIOTECH PHARMACEUTICALS LIMITED

Patent: WO2006/67794 A1, 2006 ; Location in patent: Page/Page column 21 ; Title/Abstract Full Text Show Details

6.C:

In a three necked 500 ml. round bottom flask equipped with thermo controller, stirrer and condenser was charged with N-benzoyl desoxy ephedrine (50 grams, 0.1976 mole) and 1 :1 aq. HCl (250 ml). The reaction mixture was refluxed (reaction temperature 104 - 1050C) while stirring for 13 hours. Cooled the reaction mass to 600C and extracted with chloroform to remove neutral impurities. Aqueous layer was basified with aq. Sodium hydroxide and extracted with diisopropyl ether (2 X 200 ml). The organic layers were pooled and washed with water and dried over sodium sulphate. Solvent was removed by distillation under vacuum, which afforded methamphetamine as a pale yellow to white clear liquid. (21.0 grams, 71 percent yield), Specific optical rotation.: +17.4° (2percent solution in 1.2N HCl); purity : (GLC: 98.99percent)

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With phosphorus; hydrogen iodide

Ogata; zit. bei Emde

Helvetica Chimica Acta, 1929 , vol. 12, p. 373 Full Text Show Details

Rx-ID: 333846 Find similar reactions

With ammonia; lithium in water

Birch Reduction; Hide Experimental Procedure

GLOTELL PRODUCTS, INC.; BICKETT, Tim; EITER, Frank

Patent: WO2005/32458 A2, 2005 ; Location in patent: Page/Page column 32-33 ; Title/Abstract Full Text Show Details

In a controlled laboratory setting, 12 microliters of the commercial product marketed AS"KEYACIDTM Rhodamine WT"and manufactured by Keystone Analine Corporation of Chicago, Illinois, which is a 21.2percent w/w solution of rhodamine WT in water, and 300 ML of anhydrous ammonia were combined in a flask. This is approximately equivalent to 2 oz OF KEYACID Rhodamine WT in one ton of liquid anhydrous ammonia. The mixture was stirred until a solution formed that had a very slight yellow tint. The solvation of rhodamine WT in ammonia transformed the rhodamine WT into a nearly colorless composition. The surface of each piece of equipment used in this process, however, was visibly stained a light pink in areas exposed to the ammonia and from which the ammonia had evaporated. The solution was also purposefully put in contact with various additional equipment and materials, including metal screwdriver heads, concrete, and paper. All exposed equipment and materials were visibly stained pink upon evaporation of the anhydrous ammonia. During the mixing process, some of the mixture unintentionally contacted items, including protective gloves and the hands of the researchers who were performing the mixing. These additional items were also visibly stained pink. [0071] The solution of dye in ammonia was added to 2 grams of pure pharmaceutical grade ephedrine in a 500 mL beaker. The contents of the flask were stirred to dissolve the ephedrine. Any material that came into contact with this solution, including the flask when the flask was emptied, was also visibly stained pink upon evaporation of the ammonia solvent. The visible pink stain on the flask was transferred to a sponge when the flask was washed. [0072] Lithium metal was added to the ephedrine solution. This mixture was heated to carry out a so-called"Birch"reaction. During the Birch reaction, materials contacted by the mixture were not stained. It is believed that the lack of a stain at this stage may be due to a reduction of the rhodamine WT to a colorless composition. [0073] Evaporation of the ammonia from the Birch reaction mixture left a free base form of methamphetamine. In order to purify it, the free base methamphetamine was dissolved into a liquid ether and converted to the hydrochloride salt by bubbling hydrogen chloride gas through the solution. The methamphetamine salt precipitated from solution. During this process plastic tubes used to carry the hydrogen chloride gas into the dissolved methamphetamine were visibly stained pink as was the beaker. [0074] The methamphetamine salt product was filtered through a coffee filter to retain the methamphetamine. The coffee filter used for this filtration along with the resultant product is shown in the picture of FIG. 3. Two things were observed. First, the coffee filter and resulting product are both stained pink. Further, the filtration does not occur easily because instead of a rapidly-drying, clear crystal being formed, the product was a pink sludge, which was difficult to filter and dry. This pink sludge (methamphetamine) visibly stained objects with which it came into contact pink, including plastic storage bags. A

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B: 9%

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Rx-ID: 24305408 Find similar reactions

BASF Aktiengesellschaft

Patent: US6054487 A1, 2000 ;

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Title/Abstract Full Text Show Details

12:3-(2-Benzyl-benzenesulfonylamino)-4-oxo-butyric acid

EXAMPLE 12 3-(2-Benzyl-benzenesulfonylamino)-4-oxo-butyric acid Diphenylmethane-2-sulfonyl chloride was employed to acylate the amine of Asp(OtBu)-NMe(OMe); from the resulting sulfonamide, final productproduct was obtained as a colorless foam (62 mg, 9percent) employing the methods previously described in Example 1. 1 H NMR (CD3 OD) as the lactol 8.00 (dd, 1H), 7.42 (t, 1H), 7.25 (m, 6H), 7.05 (dd, 1H), 4.54, 4.50 (d, 1H), 4.01 (s, 2H), 3.63 (m, 1H), 2.58 (m, 1H), 2.37 (m, 1H); MS

CI+1percent NH3 in CH4 304 (M-CHO)+. A

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B: 15%

Rx-ID: 24305409 Find similar reactions

BASF Aktiengesellschaft

Patent: US6054487 A1, 2000 ;

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Title/Abstract Full Text Show Details

14:4-Oxo-3-(2-p-tolyloxy-benzenesulfonylamino)-butyric acid

EXAMPLE 14 4-Oxo-3-(2-p-tolyloxy-benzenesulfonylamino)-butyric acid (4'-Methylphenyl) phenylether-2-sulfonyl chloride was employed to acylate the amine of Asp(OtBu)-NMe(OMe); from the resulting sulfonamide, final productproduct was obtained as a colorless foam (152 mg, 15percent) employing the methods previously described in Example 1. 1 H NMR (CD3 OD) as the lactol 7.90 (d, 1H), 7.48 (d, 1H), 7.35-7.00 (m, 5H), 6.80 (d, 1H), 4.55, 4.50 (d, 1H), 3.75 (m, 1H), 2.70-2.42 (m, 2H), 2.35 (s, 3H); MS

APCI probe temperature. 450° C., cone voltage 25 volts, acetonitrile: methanol 4:1, 363.1 (M+H)+. A

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B: 22%

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15:3-[2-(4-Isopropyl-phenoxy)-benzenesulfonylamino]-4-oxo-butyric acid

Rx-ID: 24305410 Find similar reactions

BASF Aktiengesellschaft

Patent: US6054487 A1, 2000 ; Title/Abstract Full Text Show Details

EXAMPLE 15 3-[2-(4-Isopropyl-phenoxy)-benzenesulfonylamino]-4-oxo-butyric acid (4'-Isopropylphenyl)phenylether-2-sulfonyl chloride was employed to acylate the amine of Asp(OtBu)-NMe(OMe); from the resulting sulfonamide, final productproduct was obtained as a colorless foam (248 mg, 22percent) employing the methods previously described in Example 1. 1 H NMR (CD3 OD) as the lactol 7.92 (d, 1H), 7.50 (t, 1H), 7.32 (m, 2H), 7.13 (m, 3H), 6.82 (d, 1H), 4.58, 4.52 (d, 1H), 3.75 (m, 1H), 2.95 (m, 1H), 2.70-2.42

(m, 2H), 1.25 (d, 6H); MS APCI probe temperature 450° C., cone voltage 25 volts, acetonitrile: methanol 4:1, 392.4 (M+H)+. A

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B: 8%

Rx-ID: 24305411 Find similar reactions

BASF Aktiengesellschaft

Patent: US6054487 A1, 2000 ;

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Title/Abstract Full Text Show Details

16:4-Oxo-3-(2-m-tolyloxy-benzenesulfonylamino)-butyric acid

EXAMPLE 16 4-Oxo-3-(2-m-tolyloxy-benzenesulfonylamino)-butyric acid (3'-Methylphenyl) phenylether-2-sulfonyl chloride was employed to acylate the amine of Asp(OtBu)-NMe(OMe); from the resulting sulfonamide, final productproduct was obtained as a colorless foam (85 mg, 8percent) employing the methods previously described in Example 1. 1 H NMR (CD3 OD) as the lactol 7.90 (d, 1H), 7.50 (t, 1H), 7.35-7.13 (m, 2H), 7.10-6.80 (m, 4H), 4.58-4.52 (d, 1H), 3.76 (m, 1H), 2.65-2.42 (m, 2H), 2.35 (s,

3H); MS APCI probe temperature 450° C., cone voltage 25 volts, acetonitrile: methanol 4:1, 363.1 (M+H)+. A

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B: 29%

Rx-ID: 24305413 Find similar reactions

BASF Aktiengesellschaft

Patent: US6054487 A1, 2000 ;

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Title/Abstract Full Text Show Details

17:3-[2-(3-Isopropyl-phenoxy)-benzenesulfonylamino]-4-oxo-butyric acid

EXAMPLE 17 3-[2-(3-Isopropyl-phenoxy)-benzenesulfonylamino]-4-oxo-butyric acid (3'-Isopropylphenyl) phenylether-2-sulfonyl chloride was employed to acylate the amine of Asp(OtBu)-NMe(OMe); from the resulting sulfonamide, final productproduct was obtained as a colorless foam (334 mg, 29percent) employing the methods previously described in Example 1. 1 H NMR (CD3 OD) as the lactol 7.90 (d, 1H), 7.50 (t, 1H), 7.45 (m, 1H), 7.25-6.80 (m, 5H), 4.58, 4.52 (d, 1H), 3.78 (m, 1H), 2.90 (m, 1H), 2.70-2.40 (m, 2H),

1.25 (d, 6H); MS APCI probe temperature 450° C., cone voltage 25 volts, acetonitrile: methanol 4:1, 392.5 (M+H)+. A

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Rx-ID: 24305415 Find similar reactions

BASF Aktiengesellschaft

Patent: US6054487 A1, 2000 ;

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Title/Abstract Full Text Show Details

11:3-Benzenesulfonylamino-4-oxo-butyric acid

EXAMPLE 11 3-Benzenesulfonylamino-4-oxo-butyric acid Benzenesulfonyl chloride was employed to acylate the amine of Asp(OtBu)-NMe(OMe); from the resulting sulfonamide, final productproduct was obtained as a colorless foam employing the methods previously described in Example 1. 1 H NMR (CD3 OD) as the lactol 7.87 (m, 2H), 7.58 (m, 3H), 4.44, 4.38 (d, 1H), 3.74 (m, 1H), 2.57 (m, 1H), 2.27 (m, 1H); MS CI+1percent NH3 in CH4 240 (M-OH)+. A

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B: 7%

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Rx-ID: 24320599 Find similar reactions

BASF Aktiengesellschaft

Patent: US6054487 A1, 2000 ; Title/Abstract Full Text Show Details

13:4-Oxo-3-(2-phenoxy-benzenesulfonylamino)-butyric acid

EXAMPLE 13 4-Oxo-3-(2-phenoxy-benzenesulfonylamino)-butyric acid Diphenylether-2-sulfonyl chloride was employed to acylate the amine of Asp(OtBu)-NMe(OMe); from the resulting sulfonamide, final productproduct was obtained as a colorless foam (72 mg, 7percent) employing the methods previously described in Example 1. 1 H NMR (CD3 OD) as the lactol 7.95 (d, 1H), 7.43 (m, 3H), 7.20 (m, 4H), 6.82 (d, 1H), 4.58, 4.52 (d, 1H), 3.75 (m, 1H), 2.70-2.40 (m, 2H); MS APCI probe temperature 450°

C., cone voltage 25 volts, acetonitrile: methanol 4:1, 350.5 (M+H)+.

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With (2S,3S)-2,3-dihydroxybutanedioic acid

Ogata

Yakugaku Zasshi, 1919 , # 451 p. 751 Chem.Abstr., 1920 , vol. 14, p. 745 Full Text Show Details

Rx-ID: 41118 Find similar reactions

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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85%

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With naphthalene; water; lithium in tetrahydrofuran

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

Rx-ID: 3822017 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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84%

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With naphthalene; water; lithium in tetrahydrofuran

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

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: 3822027 Find similar reactions

Find similar Rx-ID: 3479414 Find similar reactions

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With hydrogen; palladium on activated charcoal in methanol

Ambient temperature; Yield given. Yields of byproduct given;

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Marco, Jose L.; Royer, Jacques; Husson, Henri-Philippe

Synthetic Communications, 1987 , vol. 17, # 6 p. 669 - 676 Title/Abstract Full Text Show Details

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Multi-step reaction with 3 steps 1: 1.) LDA/HMPA / 1.) THF, -78 deg C, 20 min, 2.) -78 deg C, 1 h 2: NaBH4 / ethanol / Ambient temperature 3: hydrogen / 10percent Pd/C / methanol / Ambient temperature View Scheme

Rx-ID: 19198826 Find similar reactions

Marco, Jose L.; Royer, Jacques; Husson, Henri-Philippe

Synthetic Communications, 1987 , vol. 17, # 6 p. 669 - 676 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: NaBH4 / ethanol / Ambient temperature 2: hydrogen / 10percent Pd/C / methanol / Ambient temperature View Scheme

Rx-ID: 19212636 Find similar reactions

Marco, Jose L.; Royer, Jacques; Husson, Henri-Philippe

Synthetic Communications, 1987 , vol. 17, # 6 p. 669 - 676 Title/Abstract Full Text Show Details

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Rx-ID: 4260641 Find similar reactions

With thionyl chloride; palladium on barium sulfate; hydrogen; sodium acetate

1.) CHCl3, reflux, 3 h, 2.) AcOH; Yield given. Multistep reaction;

Noggle, F. Taylor; DeRuiter, Jack; Clark, C. Randall

Analytical Chemistry, 1986 , vol. 58, # 8 p. 1643 - 1648 Title/Abstract Full Text View citing articles Show Details

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With hydrogenchloride; hydrogen; phosphorus pentabromide; palladium on activated charcoal

Yield given. Multistep reaction;

Rx-ID: 2104711 Find similar reactions

Buckley, Thomas F.; Rapoport, Henry

Journal of the American Chemical Society, 1981 , vol. 103, # 20 p. 6157 - 6163 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 3889214 Find similar reactions

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Buckley, Thomas F.; Rapoport, Henry

Journal of the American Chemical Society, 1981 , vol. 103, # 20 p. 6157 - 6163 Title/Abstract Full Text View citing articles Show Details

in methanol; potassium hydroxide

Ambient temperature;

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Multi-step reaction with 4 steps 1: 94 percent / diethyl ether 2: H2, etheral HCl / Pd/C / 2844.3 Torr 3: H2, etheral HCl / Pd/C / 2844.3 Torr

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Rx-ID: 20566696 Find similar reactions

Buckley, Thomas F.; Rapoport, Henry

Journal of the American Chemical Society, 1981 , vol. 103, # 20 p. 6157 - 6163 Title/Abstract Full Text View citing articles Show Details

4: methanol; KOH / Ambient temperature View Scheme

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Multi-step reaction with 3 steps 1: H2, etheral HCl / Pd/C / 2844.3 Torr 2: H2, etheral HCl / Pd/C / 2844.3 Torr 3: methanol; KOH / Ambient temperature View Scheme

Rx-ID: 20577907 Find similar reactions

Buckley, Thomas F.; Rapoport, Henry

Journal of the American Chemical Society, 1981 , vol. 103, # 20 p. 6157 - 6163 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: H2, etheral HCl / Pd/C / 2844.3 Torr 2: methanol; KOH / Ambient temperature View Scheme

Rx-ID: 20578029 Find similar reactions

Buckley, Thomas F.; Rapoport, Henry

Journal of the American Chemical Society, 1981 , vol. 103, # 20 p. 6157 - 6163 Title/Abstract Full Text View citing articles Show Details

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With lithium aluminium tetrahydride

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Rx-ID: 4224865 Find similar reactions

Fowler

The Journal of organic chemistry, 1977 , vol. 42, # 15 p. 2637 - 2637 Title/Abstract Full Text View citing articles Show Details

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With palladium on activated charcoal; perchloric acid; acetic acid

Hydrogenation;

Rx-ID: 437422 Find similar reactions

Takamatsu

Yakugaku Zasshi, 1956 , vol. 76, p. 1227 Chem.Abstr., 1957 , p. 4304 Full Text Show Details

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Multi-step reaction with 3 steps 1: palladium/charcoal; aqueous methanol. HCl / Hydrogenation 3: palladium/charcoal; acetic acid; aqueous HClO4 / Hydrogenation View Scheme

Rx-ID: 22222161 Find similar reactions

Takamatsu

Yakugaku Zasshi, 1956 , vol. 76, p. 1227 Chem.Abstr., 1957 , p. 4304 Full Text Show Details

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Multi-step reaction with 2 steps 2: palladium/charcoal; acetic acid; aqueous HClO4 / Hydrogenation View Scheme

Rx-ID: 22224124 Find similar reactions

Takamatsu

Yakugaku Zasshi, 1956 , vol. 76, p. 1227 Chem.Abstr., 1957 , p. 4304 Full Text Show Details

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Rx-ID: 7989492 Find similar reactions

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Adamson et al.

Journal of the Chemical Society, 1949 , p. Spl. 144, 152 Full Text Show Details

Hydrogenation;

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Rx-ID: 97322 Find similar reactions

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With ethanol; water; aluminium

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Temmler-Werke

Patent: DE871155 , 1938 ;

Full Text Show Details

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With water; platinum

Hydrogenation;

Rx-ID: 7362651 Find similar reactions

Temmler

Patent: DE749809 , 1938 ; DRP/DRBP Org.Chem. Full Text Show Details

Temmler

Patent: DE767186 , 1937 ; DRP/DRBP Org.Chem. Full Text Show Details

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Rx-ID: 7362654 Find similar reactions

With water; platinum

Hydrogenation;

Temmler

Patent: DE749809 , 1938 ; DRP/DRBP Org.Chem. Full Text Show Details

Temmler

Patent: DE767186 , 1937 ; DRP/DRBP Org.Chem. Full Text Show Details

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Rx-ID: 842002 Find similar reactions

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With potassium hydroxide; diethyl ether

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Leithe

Chemische Berichte, 1932 , vol. 65, p. 660,665 Full Text Show Details

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Multi-step reaction with 2 steps 1: Gewinnung ueber das Lg-Hydrogentartrat 2: potassium hydroxide; diethyl ether View Scheme

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Rx-ID: 22064419 Find similar reactions

Leithe

Chemische Berichte, 1932 , vol. 65, p. 660,665 Full Text Show Details

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Hydrogenation.bei der katalytischen Hydrierung;

Rx-ID: 443669 Find similar reactions

Emde

Helvetica Chimica Acta, 1929 , vol. 12, p. 393 Full Text Show Details

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Rx-ID: 7362652 Find similar reactions

With Pd-BaSO4; sodium acetate

Hydrogenation.in neutraler Loesung;

Emde

Helvetica Chimica Acta, 1929 , vol. 12, p. 373,375,401 Full Text Show Details

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With Pd-BaSO4; sodium acetate

Hydrogenation.in neutraler Loesung;

Rx-ID: 7362653 Find similar reactions

Emde

Helvetica Chimica Acta, 1929 , vol. 12, p. 373,375,401 Full Text Show Details

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Rx-ID: 7362655 Find similar reactions

Schmidt

Archiv der Pharmazie (Weinheim, Germany), 1914 , vol. 252, p. 121 Archiv der Pharmazie (Weinheim, Germany), 1915 , vol. 253, p. 52 Full Text Show Details