(R)-N-Methyl-1-phenylpropan-2-amine [(R)-(−)-Methamphetamine] by Asch

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Reactions (40)

Yield

Substances (2)

Citations (16)

Conditions

References

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0.192 g

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Rx-ID: 11165627 Find similar reactions

With lithium aluminium tetrahydride in tetrahydrofuran

4 h; Heating;

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

With lithium aluminium tetrahydride in tetrahydrofuran

4 h; Reflux; Hide Experimental Procedure

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: 11377913 Find similar reactions

Multi-step reaction with 2 steps 1: triethylamine / CH2Cl2 / 1 h / 0 °C 2: LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

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

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: 39182466 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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Rx-ID: 39182471 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

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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: 39182506 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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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 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: 39182516 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

Synthesize Find similar Rx-ID: 39746130 Find similar reactions

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With (S)-N-isopropyl-N-methyl-2-ammonium-2'bis(pentafluorophenyl)hydroborate-1,1'-binaphthyl; hydrogen in tertbutyl 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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Synthesize Find similar Rx-ID: 9713355 Find similar reactions

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;

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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: 11375489 Find similar reactions

Multi-step reaction with 5 steps 1: triethylamine / CH2Cl2 / 0.5 h / 0 °C 2: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 3: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 4: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 5: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: water; N,N-dimethyl-formamide / 20 h / 50 °C View Scheme

Kondekar, Nagendra B.; Kumar, Pradeep

Synthetic Communications, 2011 , vol. 41, # 9 p. 1301 - 1308 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 11377446 Find similar reactions

Multi-step reaction with 6 steps 1: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: triethylamine / CH2Cl2 / 0.5 h / 0 °C 3: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 4: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 5: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 6: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: sodium tetrahydroborate / ethanol / 2 h / Reflux 2: triethylamine / dichloromethane / 0 - 20 °C 3: water; N,N-dimethyl-formamide / 20 h / 50 °C View Scheme

Kondekar, Nagendra B.; Kumar, Pradeep

Synthetic Communications, 2011 , vol. 41, # 9 p. 1301 - 1308 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1.1: (S,S)-salen-CoIII-OAc / 0.08 h / 0 °C 1.2: 8 h / 0 °C 2.1: sodium tetrahydroborate / ethanol / 2 h / Reflux 3.1: triethylamine / dichloromethane / 0 - 20 °C 4.1: water; N,N-dimethyl-formamide / 20 h / 50 °C View Scheme

Rx-ID: 30642937 Find similar reactions

Kondekar, Nagendra B.; Kumar, Pradeep

Synthetic Communications, 2011 , vol. 41, # 9 p. 1301 - 1308 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 30642940 Find similar reactions

60%

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Kondekar, Nagendra B.; Kumar, Pradeep

Synthetic Communications, 2011 , vol. 41, # 9 p. 1301 - 1308 Title/Abstract Full Text View citing articles Show Details

in water; N,N-dimethyl-formamide

T=50°C; 20 h;

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Multi-step reaction with 5 steps 1.1: sodium hydride / dimethyl sulfoxide / 1 h 1.2: 5 h / 25 °C 2.1: (S,S)-salen-CoIII-OAc / 0.08 h / 0 °C 2.2: 8 h / 0 °C 3.1: sodium tetrahydroborate / ethanol / 2 h / Reflux 4.1: triethylamine / dichloromethane / 0 - 20 °C

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Rx-ID: 30642950 Find similar reactions

Kondekar, Nagendra B.; Kumar, Pradeep

Synthetic Communications, 2011 , vol. 41, # 9 p. 1301 - 1308 Title/Abstract Full Text View citing articles Show Details

5.1: water; N,N-dimethyl-formamide / 20 h / 50 °C View Scheme

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Rx-ID: 11165625 Find similar reactions

92%

With lithium aluminium tetrahydride in tetrahydrofuran

4 h; Heating;

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

Stage #1: With lithium aluminium tetrahydride in tetrahydrofuran

T=0°C; Reflux; Stage #2: With water; sodium hydroxide in tetrahydrofuran

T=0°C; Hide Experimental Procedure

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 162 ; Title/Abstract Full Text Show Details

81:

Intermediate 81; (2/?)-Λ/-methyl-1-phenyl-2-propanamine; To a stirred suspension LiAIH4 (0.77 g, 20.4 mmol) in THF (120 ml.) was added a solution of 1 ,1-dimethylethyl [(1R)-1-methyl-2-phenylethyl]carbamate (2.4 g, 10.2 mmol) in THF(30.0ml) dropwise at 0 0C, and then the reaction mixture was heated at reflux for 2 hours.The mixture was cooled to 0 0C, and quenched by addition of ice (1.0 g), then 15percent aqueous sodium hydroxide (1.0 ml.) followed by water (0.5 ml_). The lithium salts were collected by filtration and washed with Et2O (200 ml_). The filtrate was dried (Na2SO4), filtered and concentrated. The resulting residue was distilled at reduced pressure to afford the title compound (1.6 g) as a light yellow oil. LC-MS (ES) m/z = 150 [M+H]+. A

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Synthesize Find similar Rx-ID: 29525777 Find similar reactions

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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Multi-step reaction with 4 steps 1: 70 percent / Raney-Nickel; AcOH; hydrogen / methanol / 16 h / 20 °C / 3102.97 Torr 2: 0.1 g / triethylamine / CH2Cl2 / 1 h / 0 °C 3: triethylamine / CH2Cl2 / 1 h / 0 °C 4: LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Rx-ID: 11346390 Find similar reactions

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 11347913 Find similar reactions

Multi-step reaction with 5 steps 1.1: D-proline / acetonitrile / 3 h / 0 - 20 °C 1.2: NaBH4 / acetonitrile; ethanol / 0.08 h / 0 °C 2.1: 70 percent / Raney-Nickel; AcOH; hydrogen / methanol / 16 h / 20 °C / 3102.97 Torr 3.1: 0.1 g / triethylamine / CH2Cl2 / 1 h / 0 °C 4.1: triethylamine / CH2Cl2 / 1 h / 0 °C 5.1: LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 10 steps 1.1: L-proline / dimethylsulfoxide / 2 h / 25 °C 1.2: 86 percent / NaBH4 / dimethylsulfoxide; methanol / 0.17 h / 0 °C 2.1: 88 percent / hydrogen / Pd/C / methanol / 12 h / 760.05 Torr 3.1: triethylamine / CH2Cl2 / 1 h / 0 °C 4.1: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 5.1: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 6.1: triethylamine / CH2Cl2 / 0.5 h / 0 °C 7.1: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 8.1: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 9.1: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 10.1: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 2: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 3: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 4: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Rx-ID: 11363257 Find similar reactions

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: 0.1 g / triethylamine / CH2Cl2 / 1 h / 0 °C 2: triethylamine / CH2Cl2 / 1 h / 0 °C 3: LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Rx-ID: 11374451 Find similar reactions

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 2: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

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Rx-ID: 11375283 Find similar reactions

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: aq. K2CO3 / CH2Cl2 / 0.75 h 2: 0.215 g / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

Sayyed, Iliyas Ali; Sudalai, Arumugam

Tetrahedron Asymmetry, 2004 , vol. 15, # 19 p. 3111 - 3116 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 8 steps 1: triethylamine / CH2Cl2 / 1 h / 0 °C 2: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 3: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: triethylamine / CH2Cl2 / 0.5 h / 0 °C 5: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 6: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 7: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 8: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Rx-ID: 11378923 Find similar reactions

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 7 steps 1: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 2: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: triethylamine / CH2Cl2 / 0.5 h / 0 °C 4: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 5: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 6: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 7: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Rx-ID: 11384144 Find similar reactions

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 9 steps 1: 88 percent / hydrogen / Pd/C / methanol / 12 h / 760.05 Torr 2: triethylamine / CH2Cl2 / 1 h / 0 °C 3: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 4: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 5: triethylamine / CH2Cl2 / 0.5 h / 0 °C 6: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 7: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 8: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 9: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Rx-ID: 11389304 Find similar reactions

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 2: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 3: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

Rx-ID: 11390345 Find similar reactions

Talluri, Siva Kumar; Sudalai, Arumugam

Tetrahedron, 2007 , vol. 63, # 39 p. 9758 - 9763 Title/Abstract Full Text View citing articles Show Details

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89.7%

Stage #1: With hydrogenchloride in water

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Rx-ID: 23850607 Find similar reactions

EMMELLEN BIOTECH PHARMACEUTICALS LIMITED

Patent: WO2006/67794 A1, 2006 ; Location in patent: Page/Page column 18 ;

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

Product distribution / selectivity; Hide Experimental Procedure

Title/Abstract Full Text Show Details

3.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 levmetamfetamine as a pale yellow to white clear liquid. (35 grams, 89.7percent yield), Specific optical rotation.: -17.6° (2percent solution in 1.2N HCl); purity : (GLC: 98.9percent)

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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: 23850612 Find similar reactions

EMMELLEN BIOTECH PHARMACEUTICALS LIMITED

Patent: WO2006/67794 A1, 2006 ; Location in patent: Page/Page column 20 ; Title/Abstract Full Text Show Details

5.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 levmetamfetamine as a pale yellow to white clear liquid. (20.8 grams, 71 percent yield), Specific optical rotation.: -17.2° (2percent solution in 1.2N HCl); purity : (GLC: 99percent)

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90%

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

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Rx-ID: 23850616 Find similar reactions

EMMELLEN BIOTECH PHARMACEUTICALS LIMITED

Patent: WO2006/67794 A1, 2006 ; Location in patent: Page/Page column 15-16 ; Title/Abstract Full Text Show Details

1.C:

In a three necked 500 ml. round bottom flask equipped with thermo controller, stirrer and condenser was charged with N-formyl desoxy ephedrine (50 grams, 0.28 mole) and EPO <DP n="17"/>1 :1 aq. HCl (250 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 250 ml). The organic layers were washed with water and dried over sodium sulphate. Solvent was removed by distillation under vacuum, which afforded levmetamfetamine as a pale yellow to white clear liquid. (38 grams, 90 percent yield), Specific optical rotation.: -17.4° (2percent solution in 1.2N HCl); purity : (GLC: 98.5percent)

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0.215 g

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With lithium aluminium tetrahydride in tetrahydrofuran

2 h; Heating;

Rx-ID: 9745902 Find similar reactions

Sayyed, Iliyas Ali; Sudalai, Arumugam

Tetrahedron Asymmetry, 2004 , vol. 15, # 19 p. 3111 - 3116 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1.1: 85 percent / triethylamine; thionyl chloride / 0.75 h / 0 °C 2.1: sodium azide / dimethylformamide / 6 h / 80 °C 2.2: PPh3 / acetonitrile / 6 h / Heating 2.3: ammonium formate / Pd/C / methanol / 4 h / Heating 3.1: aq. K2CO3 / CH2Cl2 / 0.75 h 4.1: 0.215 g / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

Rx-ID: 13429261 Find similar reactions

Sayyed, Iliyas Ali; Sudalai, Arumugam

Tetrahedron Asymmetry, 2004 , vol. 15, # 19 p. 3111 - 3116 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1.1: sodium azide / dimethylformamide / 6 h / 80 °C 1.2: PPh3 / acetonitrile / 6 h / Heating 1.3: ammonium formate / Pd/C / methanol / 4 h / Heating 2.1: aq. K2CO3 / CH2Cl2 / 0.75 h 3.1: 0.215 g / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

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Rx-ID: 13438449 Find similar reactions

Sayyed, Iliyas Ali; Sudalai, Arumugam

Tetrahedron Asymmetry, 2004 , vol. 15, # 19 p. 3111 - 3116 Title/Abstract Full Text View citing articles Show Details

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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: 41119 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

With L-(+)-tartaric acid

Gewinnung;

Chiang; Li

Journal of the Chinese Chemical Society (Peking), 1951 , vol. 18, p. 161 Full Text Show Details

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Synthesize Find similar Rx-ID: 3479414 Find similar reactions

With hydrogen; palladium on activated charcoal in methanol

Ambient temperature; Yield given. Yields of byproduct given;

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: 19198827 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: 19212637 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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With thionyl chloride; palladium on barium sulfate; hydrogen; sodium acetate

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

Rx-ID: 4271306 Find similar reactions

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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Rx-ID: 4271308 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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92%

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With hydrogen; palladium on activated charcoal in acetic acid

P=4413.05 Torr; 12 h; Ambient temperature;

Rx-ID: 3196292 Find similar reactions

Takashashi; Chida; Higashiyama; Onishi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 11 p. 4662 - 4670 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: 81 percent / MgSO4 / CH2Cl2 / 1 h / Ambient temperature 2: tetrahydrofuran / Ambient temperature 3: 92 percent / hydrogen / 10 percent Pd-carbon / acetic acid / 12 h / 4413.05 Torr / Ambient temperature View Scheme

Rx-ID: 20096025 Find similar reactions

Takashashi; Chida; Higashiyama; Onishi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 11 p. 4662 - 4670 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: tetrahydrofuran / Ambient temperature 2: 92 percent / hydrogen / 10 percent Pd-carbon / acetic acid / 12 h / 4413.05 Torr / Ambient temperature

Rx-ID: 20105075 Find similar reactions

Takashashi; Chida; Higashiyama; Onishi

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 11 p. 4662 - 4670 Title/Abstract Full Text View citing articles Show Details

View Scheme

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

Rx-ID: 22069700 Find similar reactions

Ogata

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