Piperidine-2-carboxylic acid [DL-Pipecolinic acid; Pipecolic acid] by Asch

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Reactions (48)

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Substances (1)

Citations (75)

Conditions

References

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With triethylamine in dichloromethane

T=25°C; 0.5 h; Solvent; Hide Experimental Procedure

Rx-ID: 5415356 Find similar reactions

Kaneka Corporation; Ohnuki, Masatoshi; Nishiyama, Akira

Patent: US2014/343289 A1, 2014 ; Location in patent: Paragraph 0055 ; Title/Abstract Full Text Show Details

4:Examples 1 to 5, Comparative Examples 1 to 5

General procedure: Triethylamine (607 mg, 6 mmol) was added to a solution of a methanesulfonic acid salt of amino acid (5 mmol), and solvent (5 mL, methanol or methylene chloride) at 25° C. In case where a solid was precipitated, the solution was stirred at 25° C. for 30 minutes after the solid was sufficiently precipitated. Thereafter, the solid was separated by filtration under reduced pressure, and was washed with the used solvent (5 mL), and was subjected to vacuum drying. The results (yields) of the operation with various amino acids are shown in the following table. Inoue,M.

Bulletin of the Chemical Society of Japan, 1962 , vol. 35, p. 1249 - 1254 Full Text View citing articles Show Details

Freifelder,M.; Stone,G.R.

Journal of Organic Chemistry, 1961 , vol. 26, p. 3805 - 3808 Full Text View citing articles Show Details

Keogh; O'Donovan

Journal of the Chemical Society [Section] C: Organic, 1970 , p. 1792 Full Text View citing articles Show Details

Israeli; Cayouette

Journal of Inorganic and Nuclear Chemistry, 1971 , vol. 33, p. 1523,1524-1527

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Brunwin et al.

Journal of the Chemical Society [Section] C: Organic, 1971 , p. 3756,3761 Full Text Show Details

Geigy Chem.

Patent: US3300482 , 1967 ; Chem.Abstr., vol. 67, # 64454 Full Text Show Details

Hemingway

Journal of Pharmacy and Pharmacology, 1968 , vol. 20, p. 87,89 Full Text Show Details

Black et al.

Australian Journal of Chemistry, 1972 , vol. 25, p. 2155,2162 Full Text Show Details

Inoue et al.

Bulletin of the Chemical Society of Japan, 1960 , vol. 33, p. 1014 Full Text Show Details

Freifelder et al.

Journal of Organic Chemistry, 1962 , vol. 27, p. 284,285 Full Text Show Details

Freifelder

Journal of Organic Chemistry, 1962 , vol. 27, p. 4046 Full Text View citing articles Show Details

Martin et al.

Journal of the American Chemical Society, 1960 , vol. 82, p. 2079 Full Text View citing articles Show Details

Wosse; Schobess

Patent: DD307710 , 1961 ; Chem.Abstr., 1966 , vol. 64, # 14139c Full Text Show Details

Geigy

Patent: NL6608673 , 1966 ; Chem.Abstr., 1967 , vol. 67, # 3106 Full Text Show Details

Geigy

Patent: US3281424 , 1964 ; Chem.Abstr., 1968 , vol. 68, # 2929u Full Text Show Details

Stamicarbon

Patent: NL6907652 , 1970 ; Full Text Show Details

Gilbertson

Phytochemistry (Elsevier), 1972 , vol. 11, p. 1737 Full Text View citing articles Show Details

Leistner et al.

Journal of the American Chemical Society, 1973 , vol. 95, p. 4040,4043, 4046, 4047 Full Text View citing articles Show Details

Yagi et al.

Journal of Biochemistry (Tokyo, Japan), 1968 , vol. 63, p. 814 Full Text View citing articles Show Details

Vakabajasi Tosio et al.

Patent: JP5134392 , 1977 ; Ref. Zh., Khim., 1978 , vol. 16, # O23P Full Text Show Details

Abbott Labor.

Patent: US3159639 , 1962 ; Chem.Abstr., 1965 , vol. 62, # 7732 Full Text Show Details

Fukumoto; Murakami

Nippon Kagaku Zasshi, 1963 , vol. 84, p. 736 Chem.Abstr., 1964 , vol. 60, # 653 Full Text Show Details

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Zhang, Rumin

Patent: US2002/103135 A1, 2002 ; Title/Abstract Full Text Show Details

wherein said analogs are selected from the group consisting of: proline; pipecolic acid; cyclohexylglycine; tert-butylglycine; D-γ-carboxyglutamic acid, and aminoadipic acid. Hide Details

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Schmitz, Robert A.

Patent: US6299892 B1, 2001 ; Title/Abstract Full Text Show Details

a,a' dichloropropionic acid ... 2,6 pyridine dicarboxylic acid quinolinic acid imidazole dicarboxylic acid maleic acid pipecolic acid

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The Upjohn Company

Patent: US5252735 A1, 1993 ; Title/Abstract Full Text Show Details

Examples of heterocylic amines corresponding to heterocyclic amine rings according to --NR9 R10 are: ... 4-phenyl-1-piperidine thiazoline, 3-piperidine methanol, 2-piperidine methanol, pipecolic acid, 3-piperidine ethanol, 2-piperidine ethanol, 1-piperazine propanol, ...

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Vertex Pharmaceuticals, Inc.

Patent: US5656627 A1, 1997 ; Title/Abstract Full Text Show Details

Preferred compounds of embodiment C of this invention are also those in which each A is independently selected from the group consisting of the α-amino acids: ... leucine, isoleucine, glutamine, methionine, homoproline, 3-(2-thienyl) alanine, and 3-(3-thienyl) alanine.

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Pharmacia and Upjohn Company

Patent: US5703075 A1, 1997 ; Title/Abstract Full Text Show Details

Examples of heterocylic amines corresponding to heterocyclic amine rings according to -NR9 N10 are: ... 4-phenyl-1-piperidine thiazolidine, 3-piperidine methanol, 2-piperidine methanol, pipecolic acid, 3-piperidine ethanol, 2-piperidine ethanol, 1-piperazine propanol, ...

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Vertex Pharmaceuticals, Inc.

Patent: US5656627 A1, 1997 ; Title/Abstract Full Text Show Details

Preferred compounds of embodiment D of this invention are also those in which A is independently selected from the group consisting of the α-amino acids: ...

leucine, isoleucine, glutamine, methionine, homoproline, 3-(2-thienyl) alanine, and 3-(3-thienyl) alanine.

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Vertex Pharmaceuticals, Incorporated

Patent: US5847135 A1, 1998 ; Title/Abstract Full Text Show Details

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Vertex Pharmaceuticals, Incorporated

Patent: US5847135 A1, 1998 ; Title/Abstract Full Text Show Details

Preferred compounds of embodiment F of this invention are also those in which A is independently selected from the group consisting the α-amino acids: ... leucine, isoleucine, glutamine, methionine, homoproline, 3-(2-thienyl)alanine, and 3-(3-thienyl)alanine.

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Vertex Pharmaceuticals, Incorporated

Patent: US5847135 A1, 1998 ; Title/Abstract Full Text Show Details

Preferred compounds of embodiment D of this invention are also those in which A is independently selected from the group consisting of the α-amino acids: ... leucine, isoleucine, glutamine, methionine, homoproline, 3-(2-thienyl)alanine, and 3-(3-thienyl)alanine.

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Vertex Pharmaceuticals, Incorporated

Patent: US5847135 A1, 1998 ; Title/Abstract Full Text Show Details

Preferred compounds of embodiment E of this invention are also those in which A is independently selected from the group consisting the α-amino acids: ... leucine, isoleucine, glutamine, methionine, homoproline, 3-(2-thienyl)alanine, and 3-(3-thienyl)alanine.

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Nippon Petrochemicals Co., Ltd.

Patent: US4656186 A1, 1987 ;

Title/Abstract Full Text Show Details

The following amino acids can also be used to prepare the di-, tri-, or where appropriate, the tetra-amino acid derivatives of the chlorins, porphyrins, or bacteriochlorins, employing the procedures of one of the aforementioned methods: Piperidine-2-carboxylic acid; Pyrrole-2-carboxylic acid; Piperidine-2-propionic acid; and Pyrrole-2-acetic acid.

Hardtmann; Goetz E.; Houlihan; William J.; Giger; Rudolf K. A.

Patent: US4760065 A1, 1988 ;

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Title/Abstract Full Text Show Details

6:(-)-8aS-1,5,6,7,8,8a-hexahydro-3-methylthioimidazo[1,5-a]pyridine STR18 Step A:

After working the tartrate salt with 10percent ammonia, the L-(-)-pipecolic acid is obtained by elution and concentration by evaporation and then once recrystallized out of a minimum of H2 O and a maximum of alcohol, [α]D20 -27.5 (C=2, H2 O).

Schmitz, Robert A.

Patent: EP1288238 A1, 2003 ;

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Title/Abstract Full Text Show Details

hypobromous acid ... 2,6 pyridine dicarboxylic acid quinolinic acid imidazole dicarboxylic acid maleic acid pipecolic acid 2,6 pyridine dicarboxylic acid dipicolinic acid lipoic acid ...

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With cadmium(II) sulphide; sodium sulfate in water

1 h; IrradiationpH 10.1; on titanium(IV) also; stereochemistry of product; tested by FTIR; Mechanism;

Ohtani, Bunsho; Yako, Takayuki; Samukawa, Yoriaki; Nishimoto, Sei-Ichi; Kanamura, Kiyoshi

Chemistry Letters, 1997 , # 1 p. 91 - 92 Title/Abstract Full Text View citing articles Show Details

With dihydrogen hexachloroplatinate; Titanium(IV) oxide in water

T=24.85°C; Irradiation; Kinetics; Further Variations:Reagents;

Ikeda; Sugiyama; Pal; Marci; Palmisano; Noguchi; Uosaki; Ohtani

Physical Chemistry Chemical Physics, 2001 , vol. 3, # 2 p. 267 - 273 Title/Abstract Full Text View citing articles Show Details

With 1,5-dimethyl-2-phenyl-4-amino-3-pyrazolone; water; phenol; lysine oxidase; horseradish peroxidase

pH=7.5; potassium phosphate/potassium diphosphate buffer; Conversion of starting material; Hide Experimental Procedure

Friedrich, Thomas; Zimmermann, Norbert; Stuermer, Rainer

Patent: US2004/158061 A1, 2004 ; Location in patent: Page 5-6 ; Title/Abstract Full Text Show Details

3.3.a:EXAMPLE 3; Determination of the Enzymatic Activity in the Presence and Absence of Reducing Agent; 3.a; Assays with Various Substrates

The substrates employed were L-lysine monohydrochloride (for biochemical purposes, 99percent from Merck), ethanolamine from BASF AG, glycine ethyl ester, 1,8-diaminooctane from Aldrich, n-butylamine from BASF AG, 1,4-diaminobutane from BASF AG, ethylenediamine from BASF AG, spermine from Aldrich, 3aminomethylpyridine from Aldrich, benzylamine from Aldrich, L-(+)-ornithine hydrochloride (99percent from Aldrich) and 1,6-diaminohexane from BASF AG. [0106] Measurement series in each case with a concentration of 1 200, 600, 300, 150, 75, 37.5 and 18.75 μmol of (di)amine per 1 l of water were carried out in a microtiter plate. 2 measurement series were carried out in each case; one with enzyme and one without enzyme as reference. [0107] 100 μl of each of the diluted solutions were taken. To this solution were added 25 μl of lysine oxidase and 40 μl of 35 millimolar phenol solution in 200 millimolar potassium phosphate/potassium diphosphate

solution with a pH of 7.5, 40 μl of a 2 millimolar aqueous 4-aminoantipyrine solution and 40 μl of a solution of 0.35 mg of peroxidase (horseradish from Sigma) in 1 ml of water. [0108] In the reference measurement series, the 25 μl of lysine oxidase were replaced by 25 μl of water. A violet dye was formed by the ammonia produced on conversion of the substrates and its absorption in the UV at 500 nm was measured (T. Uwajima, O. Terada, Methods in Enzymology 1982, 89, 243 ff.). [0109] The relative conversion rates of the substrates compared with L-lysine are to be found in table 1. It emerged that both (un)substituted aliphatic amines and diamines, and amino acids and their derivatives can be converted in the presence of lysine oxidase. Remarkably, the conversion rate of some substrates is increased by comparison with L-lysine. The use of derivatives of lysine and ornithine is of particular interest in relation to the preparation of piperidine-2-carboxylic acid and proline derivatives. Hide Details

With water; lysine oxidase

pH=7; Conversion of starting material; Hide Experimental Procedure

Friedrich, Thomas; Zimmermann, Norbert; Stuermer, Rainer

Patent: US2004/158061 A1, 2004 ; Location in patent: Page 6 ; Title/Abstract Full Text Show Details

3.3.b:3.b; Assay with Various Concentrations of Reducing Agent

In order to test the tolerance of lysine oxidases to reducing agents, by way of example the measurement series with L-lysine using the lysine oxidase from Pichia pastoris was repeated in the presence of 0.001percent by weight, 0.01percent by weight, 0.1percent by weight, 0.5percent by weight and 1percent by weight of NaBH4 based on the total amount of substrate solution. The results are to be found in table 2. It emerged that the activity of the lysine oxidase remained virtually unchanged up to a concentration of 0.1percent by weight NaBH4. At concentrations of 0.5percent by weight NaBH4, the activity decreased because of the increase in the pH. Relatively good conversions were still achieved up to an NaBH4 concentration of 1percent by weight. Thus 1percent by weight NaBH4, based on the total amount of the substrate solution, was employed in each of the subsequent tests.

With sodium tetrahydroborate; water; lysine oxidase

pH=7 - 10; Conversion of starting material; Hide Experimental Procedure

Friedrich, Thomas; Zimmermann, Norbert; Stuermer, Rainer

Patent: US2004/158061 A1, 2004 ; Location in patent: Page 6 ; Title/Abstract Full Text Show Details

3.3.b:3.b; Assay with Various Concentrations of Reducing Agent

Stage #1: With water; lysine oxidase

Friedrich, Thomas; Zimmermann, Norbert; Stuermer, Rainer

Patent: US2004/158061 A1, 2004 ; Location in patent: Page 6 ;

Stage #2: With sulfuric acid in ethanol

T=20°C; Stage #3: With benzyl chloroformate; triethylamine

T=20°C; 3 h; Conversion of starting material; Hide Experimental Procedure

Title/Abstract Full Text Show Details

3.3.c:3.c; Workup of the Samples

50 ml of a 1.2 millimolar L-lysine solution converted in the presence of lysine oxidase was evaporated to dryness, taken up in five times the amount of ethanol, mixed with 1 drop of concentrated sulfuric acid and left to stand at room temperature overnight. After removal of the ethanol by distillation in vacuo, the residue was mixed with an excess of triethylamine and benzyl chloroformate and left to react at room temperature for 3 h. After addition of water, the N-benzyloxycarbonyl derivatives wee extracted with dichloromethane. The organic phase was characterized by mass spectrometry and NMR. The resulting spectra corresponded to those of authentic samples of piperidine-2-carboxylic acid.

With Cp*Ir(biot-p-L)Cl; L-amino acid oxidase from Crotalus atrox; oxygen; sodium formate; catalase from bovine liver in aq. buffer T=37°C; pH=7.8; Enzymatic reaction; Hide Experimental Procedure

Koehler; Wilson; Duerrenberger; Ghislieri; Churakova; Quinto; Knoerr; Haeussinger; Hollmann; Turner; Ward

Nature Chemistry, 2013 , vol. 5, # 2 p. 93 - 99 Title/Abstract Full Text View citing articles Show Details

Typical procedure for a double stereoselective deracemization with MAON/ATHase (analytical scale).

General procedure: The following stock solutions were prepared. Catalase from bovine liver (50 kU ml-1) was dissolved in MOPS/sodium formate buffer (0.6 M in MOPS, 3.0 M in sodium formate, pH adjusted with aq. KOH to pH 7.8). Sav S112T (16.4 mg ml-1, 0.75 mM free binding sites, assuming three free binding sites per tetramer) was dissolved in the catalase containing buffer. [IrCp*(biot-p-L)Cl] was dissolved in DMF (37.5 mM). Affinity purified MAO-N-9 (buffer exchange with MOPS, 0.6 M, pH adjusted with KOH to 7.8) was diluted in MOPS buffer (0.6 M, pH adjusted with KOH to 7.8) to a concentration of 0.38 mg ml-1. Substrate stock was prepared by dissolving the hydrochloride of 1-ox in H2O (1 M). The ATHase was prepared by adding [IrCp*(biot-p-L)Cl]-stock (10 μl ml-1) to the Sav-stock solution. MAO-N-stock was placed in 1.5 ml PP-tubes (100 μl) and ATHase was added (100 μl). The reactions were initiated by addition of substrate stock solution (7.5 μl) and incubated at 37 °C and 250 r.p.m. in a lying position. For work-up aq. NaOH solution was added (50 μl of a 10 M solution) and the mixture extracted with CH2Cl2 (1 × 1 ml). The organic phase was dried over Na2SO4 and analysed by HPLC (Supplementary Sections S2.3.1 and S2.4.1).

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Multi-step reaction with 3 steps 1.1: tri-n-butyl-tin hydride / toluene / 4 h / 130 °C 1.2: 80 °C 2.1: sodium periodate; RuCl3*2H2O / tetrachloromethane; water; acetonitrile / 0.5 h / 20 °C 3.1: naphthalene; sodium / tetrahydrofuran / 0.75 h / -78 °C View Scheme

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89%

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Rx-ID: 32628112 Find similar reactions

With naphthalene; sodium in tetrahydrofuran

T=-78°C; 0.75 h;

Reddy, Basi V. Subba; Chaya, Dudhmal N.; Yadav, Jhillu S.; Gree, Rene

Synthesis, 2012 , vol. 2012, # 2 p. 297 - 303 Title/Abstract Full Text View citing articles Show Details

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Reddy, Basi V. Subba; Chaya, Dudhmal N.; Yadav, Jhillu S.; Gree, Rene

Synthesis, 2012 , vol. 2012, # 2 p. 297 - 303 Title/Abstract Full Text View citing articles Show Details

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100%

With (R)-1-[(S)-2(dicyclohexylphosphino)ferrocenyl]ethyldiphenylphosphine; hydrogen; bis(norbornadiene)rhodium(I) tetrafluoroborate in methanol

T=60°C; P=75006 Torr; 20 h; Product distribution; Further Variations:ReagentsSolventsratio;

Studer, Martin; Wedemeyer-Exl, Christina; Spindler, Felix; Blaser, Hans-Ulrich

Monatshefte fur Chemie, 2000 , vol. 131, # 12 p. 1335 - 1343 Title/Abstract Full Text View citing articles Show Details

99%

With hydrogen; platinum(IV) oxide in ethanol

T=125°C; P=18751.5 Torr; 1 h; Irradiationmicrowave irradiation;

Heller, Eberhard; Lautenschlaeger, Werner; Holzgrabe, Ulrike

Tetrahedron Letters, 2005 , vol. 46, # 8 p. 1247 - 1249 Title/Abstract Full Text View citing articles Show Details

99%

With hydrogen; platinum(IV) oxide in ethanol

T=80°C; P=5171.62 Torr; 0.166667 h; microwave irradiation;

Vanier, Grace S.

Synlett, 2007 , # 1 p. 131 - 135 Title/Abstract Full Text View citing articles Show Details

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97%

With palladium 10 on activated carbon; hydrogen in water

T=80°C; P=750.075 Torr; Continuous flow;

Irfan, Muhammed; Petricci, Elena; Glasnov, Toma N.; Taddei, Maurizio; Kappe, C. Oliver

European Journal of Organic Chemistry, 2009 , # 9 p. 1327 - 1334 Title/Abstract Full Text View citing articles Show Details

With hydrogen; acetic acid; platinum

T=40°C; P=2280 Torr;

Hess; Leibbrandt

Chemische Berichte, 1917 , vol. 50, p. 386 Chemische Berichte, 1919 , vol. 52, p. 210 Full Text Show Details

With ammonium hydroxide; hydrogen; palladium on activated charcoal

With ethanol; acetic acid

T=80°C; Hydrogenation;

af Ekenstam et al.

Acta Chemica Scandinavica (1947-1973), 1957 , vol. 11, p. 1183,1184 Full Text Show Details

With acetic acid; platinum

T=20°C; Hydrogenation;

Sorm

Collection of Czechoslovak Chemical Communications, 1948 , vol. 13, p. 57,68 Full Text Show Details

With ethanol; sodium

Mende

Chemische Berichte, 1896 , vol. 29, p. 2887 Full Text Show Details

Ladenburg

Chemische Berichte, 1891 , vol. 24, p. 640 Anm. Full Text Show Details

With n-pentan-1-ol; sodium

Clemo; Ramage

Journal of the Chemical Society, 1931 , p. 437,441 Full Text Show Details

Morrison

Biochemical Journal, 1953 , vol. 53, p. 474,476 Full Text Show Details

10 g (95%)

With ammonium hydroxide; palladium monocarbide in water

Warner-Lambert

Patent: US6251919 B1, 2001 ;

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11.1:{4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-[1-(3-methyl-butyl)-piperidin-2-yl]-methanone

Step 1: The preparation of piperidine-2-carboxylic acid: Pyridine-2-carboxylic acid (10.0 g, 81.3 mmol) was treated with H2O (100 mL), NH4OH (10 mL), and 20percent Pd/C (2.0 g) and shaken under an atmosphere of H2. The reaction was filtered and concentrated to give 10 g (95percent) of the desired product. MS: 130 (M+1 for C6H11N1O2).

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Hu, Lain-Yen; Ryder, Todd R.; Nikam, Sham S.; Millerman, Elizabeth; Szoke, Balazs G.; Rafferty, Michael F.

Bioorganic and Medicinal Chemistry Letters, 1999 , vol. 9, # 8 p. 1121 - 1126 Title/Abstract Full Text View citing articles Show Details

43%

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With hydrogen; palladium on activated carbon in water

T=200°C; P=5171.62 Torr; 8 h; Product distribution / selectivity; Hide Experimental Procedure

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BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; MICROBIA, INC.

Patent: WO2008/103366 A2, 2008 ; Location in patent: Page/Page column 17, 19 ; Title/Abstract Full Text Show Details

Hydrodenitrogenation of L-Lysine in Water. L-Lysine hydrochloride (1.83 g, 10 mmol), water (100 mL) and Raney Ni (0.58 g, 10 mmol) are added to the reaction chamber of a Parr high-pressure reactor and the vessel is assembled. The reaction chamber is flushed for 10 min with Ar and then pressurized with H2 to 100 psi (689.48 kPa). The reaction chamber's outlet valve is then opened to the atmosphere. This process is repeated two additional times. After repressurizing the reaction vessel with 100 psi of H2, the temperature of the stirred reaction vessel is increased to 2000C, which results in a reaction pressure of 300 psi. The reaction is held at 2000C for 8 h. Upon cooling to rt (room temperature), the pressurized reaction vessel's H2 is vented in a fume hood. After filtration, the reaction solution is concentrated.

33%

With hydrogen; nickel in water

T=200°C; P=5171.62 - 51716.2 Torr; 8 h; Product distribution / selectivity; Hide Experimental Procedure

BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; MICROBIA, INC.

Patent: WO2008/103366 A2, 2008 ; Location in patent: Page/Page column 17, 19 ; Title/Abstract Full Text Show Details

8 h. Upon cooling to rt (room temperature), the pressurized reaction vessel's H2 is vented in a fume hood. After filtration, the reaction solution is concentrated.

18%

With hydrogen; 5 activated charcoal-supported ruthenium catalyst in water

T=200°C; P=5171.62 - 51716.2 Torr; 8 h; Product distribution / selectivity; Hide Experimental Procedure

BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; MICROBIA, INC.

Patent: WO2008/103366 A2, 2008 ; Location in patent: Page/Page column 17, 19 ; Title/Abstract Full Text Show Details

With hydrogen; platinum on carbon in water

T=200°C; P=5171.62 Torr; 8 h; Product distribution / selectivity; Hide Experimental Procedure

BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; MICROBIA, INC.

Patent: WO2008/103366 A2, 2008 ; Location in patent: Page/Page column 17, 19 ; Title/Abstract Full Text Show Details

8 h. Upon cooling to rt (room temperature), the pressurized reaction vessel's H2 is vented in a fume hood. After filtration, the reaction solution is concentrated.

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T=420°C; Kinetics; Further Variations:TemperaturesPressures;

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Rosas, Felix; Monsalve, Angiebelk; Tosta, Maria; Herize, Armando; Dominguez, Rosa M.; Brusco, Doris; Chuchani, Gabriel

International Journal of Chemical Kinetics, 2005 , vol. 37, # 6 p. 383 - 389 Title/Abstract Full Text View citing articles Show Details

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RIKEN

Patent: EP1588709 A1, 2005 ; Location in patent: Page/Page column 20 ;

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Darwin Discovery Limited

Patent: US6156900 A1, 2000 ;

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1:EXAMPLE 1

EXAMPLE 1 (R)-N-acetylpipecolic acid was placed in 10 volumes of toluene and heated, with stirring, to reflux. On attaining reflux, a catalytic amount of 4-toluenesulphonic acid was added to the solution which was then left to reflux for two hours with stirring. After this time had elapsed, the toluene was removed by rotary evaporation. To the residual solid was added 10 volumes of distilled water; this was then extracted with methyl ethyl ketone (MEK) (3*10 vols) to leave the sulphonic acid in the aqueous layer with any pipecolic acid formed. The MEK extracts were then concentrated down to a solid on the rotary evaporator to give racemic-N-acetylpipecolic acid, with 97percent recovery. A

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With Cu complex of polymer from 2,6-bis-aminomethylpyridine and 4,4'-bisaminomethyldiphenylmethane; water in dimethyl sulfoxide

T=25°C; var.reag.: Cu(2+) complex of 2,6-bis-benzylaminomethylpyridine; oligomers of 2,6-bisaminomethylpyridine and 4,4'-bis-aminomethyldiphenylmethane; Rate constant;

Scrimin, Paolo; Tecilla, Paolo; Tonellato, Umberto

European Journal of Organic Chemistry, 1998 , # 6 p. 1143 - 1153 Title/Abstract Full Text View citing articles Show Details

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With sodium hydroxide in water

3 h; Heating;

Rx-ID: 4710944 Find similar reactions

Myers, Andrew G.; Gleason, James L.; Yoon, Taeyoung; Kung, Daniel W.

Journal of the American Chemical Society, 1997 , vol. 119, # 4 p. 656 - 673 Title/Abstract Full Text View citing articles Show Details

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With hydrogen; palladium on activated charcoal in methanol

Yield given. Yields of byproduct given;

Hashimoto, Kimiko; Higashibayashi, Shuhei; Shirahama, Haruhisa

Heterocycles, 1997 , vol. 46, # 1 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details

With hydrogen; palladium on activated charcoal in hydrogenchloride

Yield given. Yields of byproduct given;

Hashimoto, Kimiko; Higashibayashi, Shuhei; Shirahama, Haruhisa

Heterocycles, 1997 , vol. 46, # 1 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details

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With Pt on TiO2 in water

Irradiationdifferent Pt loading of catalyst; Rate constant;

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Ohtani, Bunsho; Iwai, Kunihiro; Nishimoto, Sei-Ichi; Sato, Shinri

Journal of Physical Chemistry B, 1997 , vol. 101, # 17 p. 3349 - 3359 Title/Abstract Full Text View citing articles Show Details

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With cadmium(II) sulphide in water

T=24.9°C; Irradiationvarious time, catalysts, also in D2O; further amino acids; Rate constantProduct distributionMechanism;

Ohtani, Bunsho; Kawaguchi, Jun-ichi; Kozawa, Masami; Nishimoto, Sei-ichi; Inui, Tomoyuki; Izawa, Kunisuke

Journal of the Chemical Society, Faraday Transactions, 1995 , vol. 91, # 7 p. 1103 - 1110 Title/Abstract Full Text View citing articles Show Details

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With potassium hydroxide in methanol

2 h; Ambient temperature;

Rx-ID: 2484143 Find similar reactions

Landini, Dario; Penso, Michele

Journal of Organic Chemistry, 1991 , vol. 56, # 1 p. 420 - 423 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 52 percent / K2CO3 / benzyltriethylammonium chloride / acetonitrile / 20 h / Heating 2: 20percent aq. KOH / methanol / 2 h / Ambient temperature View Scheme

Landini, Dario; Penso, Michele

Journal of Organic Chemistry, 1991 , vol. 56, # 1 p. 420 - 423 Title/Abstract Full Text View citing articles Show Details

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100%

With hydrogen; platinum(IV) oxide in water

T=60°C; P=3102.9 Torr; 5 h;

Shuman, Robert T.; Ornstein, Paul L.; Paschal, Jonathan W.; Gesellchen, Paul D.

Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 738 - 741 Title/Abstract Full Text View citing articles Show Details

With water; platinum

Hydrogenation;

Beyerman

Recueil des Travaux Chimiques des Pays-Bas, 1959 , vol. 78, p. 134,137 Full Text Show Details

Stevens; Ellman

Journal of Biological Chemistry, 1950 , vol. 182, p. 75,76 Full Text Show Details

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Synthesize Find similar Rx-ID: 2235215 Find similar reactions

With hydrogen; platinum(IV) oxide in ethanol; water

T=60°C; P=3102.9 Torr; 24 h; Yields of byproduct given. Title compound not separated from byproducts;

Shuman, Robert T.; Ornstein, Paul L.; Paschal, Jonathan W.; Gesellchen, Paul D.

Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 738 - 741 Title/Abstract Full Text View citing articles Show Details

With hydrogen; platinum(IV) oxide in ethanol; water

T=60°C; P=3102.9 Torr; 24 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Shuman, Robert T.; Ornstein, Paul L.; Paschal, Jonathan W.; Gesellchen, Paul D.

Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 738 - 741 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 4 steps 1: 30percent hydrogen peroxide / acetic acid / 24 h / Heating 2: dimethylcarbamyl chloride / CH2Cl2 / 24 h / Ambient temperature 3: 71 percent / 6 N HCl / 24 h / Heating 4: hydrogen / platinum oxide / ethanol; H2O / 24 h / 60 °C / 3102.9 Torr View Scheme

Rx-ID: 21936522 Find similar reactions

Shuman, Robert T.; Ornstein, Paul L.; Paschal, Jonathan W.; Gesellchen, Paul D.

Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 738 - 741 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: dimethylcarbamyl chloride / CH2Cl2 / 24 h / Ambient temperature 2: 71 percent / 6 N HCl / 24 h / Heating 3: hydrogen / platinum oxide / ethanol; H2O / 24 h / 60 °C / 3102.9 Torr View Scheme

Rx-ID: 21937043 Find similar reactions

Shuman, Robert T.; Ornstein, Paul L.; Paschal, Jonathan W.; Gesellchen, Paul D.

Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 738 - 741 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 71 percent / 6 N HCl / 24 h / Heating 2: hydrogen / platinum oxide / ethanol; H2O / 24 h / 60 °C / 3102.9 Torr View Scheme

Rx-ID: 21974143 Find similar reactions

Shuman, Robert T.; Ornstein, Paul L.; Paschal, Jonathan W.; Gesellchen, Paul D.

Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 738 - 741 Title/Abstract Full Text View citing articles Show Details

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89%

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With hydrogen; palladium on activated charcoal

Rx-ID: 2431680 Find similar reactions

Murahashi, Shun-Ichi; Shiota, Tatsuki

Tetrahedron Letters, 1987 , vol. 28, # 51 p. 6469 - 6472 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: 1.) H2O2(30percent)/Na2WO4*2H2O, 2.) 4 N aq.HCl / 1.) water or methanol; 2.) water 2: 86 percent / H2O / aq. HCl / 100 °C 3: 89 percent / H2 / Pd/C View Scheme

Rx-ID: 21590195 Find similar reactions

Murahashi, Shun-Ichi; Shiota, Tatsuki

Tetrahedron Letters, 1987 , vol. 28, # 51 p. 6469 - 6472 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 86 percent / H2O / aq. HCl / 100 °C 2: 89 percent / H2 / Pd/C View Scheme

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Rx-ID: 21625109 Find similar reactions

Murahashi, Shun-Ichi; Shiota, Tatsuki

Tetrahedron Letters, 1987 , vol. 28, # 51 p. 6469 - 6472 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1932725 Find similar reactions

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With sodium hydride

1.) water, 25 deg C, 10 min; 2.) water, 80 deg C, 3 h; further solv., var. temp. and time; Yield given. Multistep reaction;

Katritzky, Alan R.; Yang, Yu-Kun

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1984 , p. 885 - 890 Title/Abstract Full Text Show Details

With sodium hydride

1.) water, 25 deg C, 10 min; 2.) water, 80 deg C, 3 h; further solv., var. temp. and time; Yield given. Yields of byproduct given;

Katritzky, Alan R.; Yang, Yu-Kun

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1984 , p. 885 - 890 Title/Abstract Full Text Show Details

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Synthesize Find similar Rx-ID: 1952050 Find similar reactions

A: 8 % Chromat. B: 44 % Chromat.

With Cu2Cl2; ammonium hydroxide; (NH4)2CO3

T=125°C; 24 h; Title compound not separated from byproducts;

Effenberger, Franz; Drauz, Karlheinz; Foerster, Siegfried; Mueller, Wolfgang

Chemische Berichte, 1981 , vol. 114, # 1 p. 173 - 189 Title/Abstract Full Text Show Details

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With NH4I; 1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane; ammonia in water

Rx-ID: 2012832 Find similar reactions

Effenberger, Franz; Drauz, Karlheinz; Foerster, Siegfried; Mueller, Wolfgang

Chemische Berichte, 1981 , vol. 114, # 1 p. 173 - 189

T=70 - 80°C; 3 h;

Title/Abstract Full Text Show Details

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93 % Chromat.

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With ammonium hydroxide

T=100°C; 12 h;

Rx-ID: 2324603 Find similar reactions

Effenberger, Franz; Drauz, Karlheinz; Foerster, Siegfried; Mueller, Wolfgang

Chemische Berichte, 1981 , vol. 114, # 1 p. 173 - 189 Title/Abstract Full Text Show Details

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34 % Chromat.

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With ammonium hydroxide

74 h; Ambient temperaturefurther reagent: 1N NaOH;

Rx-ID: 2324607 Find similar reactions

Effenberger, Franz; Drauz, Karlheinz; Foerster, Siegfried; Mueller, Wolfgang

Chemische Berichte, 1981 , vol. 114, # 1 p. 173 - 189 Title/Abstract Full Text Show Details

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55%

acid hydrolysis;

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Rx-ID: 2741876 Find similar reactions

Asher, Vikram; Becu, Christian; Anteunis, Marc J. O.; Callens, Roland

Tetrahedron Letters, 1981 , vol. 22, p. 141 - 144 Title/Abstract Full Text View citing articles Show Details

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58 % Chromat.

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With ammonium hydroxide

74 h; Ambient temperature;

Rx-ID: 2981787 Find similar reactions

Effenberger, Franz; Drauz, Karlheinz; Foerster, Siegfried; Mueller, Wolfgang

Chemische Berichte, 1981 , vol. 114, # 1 p. 173 - 189 Title/Abstract Full Text Show Details

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47 % Chromat.

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With ammonium hydroxide

74 h; Ambient temperaturefurther reagent: 1N NaOH;

Rx-ID: 2982036 Find similar reactions

Effenberger, Franz; Drauz, Karlheinz; Foerster, Siegfried; Mueller, Wolfgang

Chemische Berichte, 1981 , vol. 114, # 1 p. 173 - 189 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: 90 percent / conc. HCl, 100percent HCOOH / H2O / 24 h / 125 °C 2: 58 percent Chromat. / conc. aq. NH3 / 74 h / Ambient temperature View Scheme

Rx-ID: 20631985 Find similar reactions

Effenberger, Franz; Drauz, Karlheinz; Foerster, Siegfried; Mueller, Wolfgang

Chemische Berichte, 1981 , vol. 114, # 1 p. 173 - 189 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: 95 percent / stannic tetrachloride 2: 55 percent / acid hydrolysis View Scheme

Rx-ID: 20635478 Find similar reactions

Asher, Vikram; Becu, Christian; Anteunis, Marc J. O.; Callens, Roland

Tetrahedron Letters, 1981 , vol. 22, p. 141 - 144 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1: 76 percent / conc. HCl, 100percent HCOOH / H2O / 24 h / 125 °C 2: 93 percent Chromat. / conc. aq. NH3 / 12 h / 100 °C View Scheme

Rx-ID: 20642842 Find similar reactions

Effenberger, Franz; Drauz, Karlheinz; Foerster, Siegfried; Mueller, Wolfgang

Chemische Berichte, 1981 , vol. 114, # 1 p. 173 - 189 Title/Abstract Full Text Show Details

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Multi-step reaction with 3 steps 1: 33 percent Chromat. / dimethylformamide / 10 h / 60 - 80 °C 2: 76 percent / conc. HCl, 100percent HCOOH / H2O / 24 h / 125 °C 3: 93 percent Chromat. / conc. aq. NH3 / 12 h / 100 °C View Scheme

Rx-ID: 20655208 Find similar reactions

Effenberger, Franz; Drauz, Karlheinz; Foerster, Siegfried; Mueller, Wolfgang

Chemische Berichte, 1981 , vol. 114, # 1 p. 173 - 189 Title/Abstract Full Text Show Details

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Multi-step reaction with 3 steps 1: 61 percent / hexamethylguanidinium cyanate / acetonitrile / 25 h / 80 °C 2: 90 percent / conc. HCl, 100percent HCOOH / H2O / 24 h / 125 °C 3: 58 percent Chromat. / conc. aq. NH3 / 74 h / Ambient temperature View Scheme

Rx-ID: 20655210 Find similar reactions

Effenberger, Franz; Drauz, Karlheinz; Foerster, Siegfried; Mueller, Wolfgang

Chemische Berichte, 1981 , vol. 114, # 1 p. 173 - 189 Title/Abstract Full Text Show Details

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Rx-ID: 1481412 Find similar reactions

A: 4.3% B: 0.1% C: 0.8% D: 2.9%

in water

T=10 - 20°C; 1 h; contact glow discharge electrolysis (500-600 V, 45 mA);

Terasawa, Jun-ichi; Harada, Kaoru

Chemistry Letters, 1980 , p. 73 - 76 Title/Abstract Full Text Show Details

A: 4.3% B: 0.1% C: 0.8% D: 2.9%

in water

T=10 - 20°C; 1 h; contact glow discharge electrolysis (500-600 V, 45 mA);

Terasawa, Jun-ichi; Harada, Kaoru

Chemistry Letters, 1980 , p. 73 - 76 Title/Abstract Full Text Show Details

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With perchloric acid; ammonium sulphamate; sodium isothiocyanate

Rx-ID: 1759384 Find similar reactions

Singer, Sandra S.; Singer, George M.; Cole, Barbara B.

T=50°C; piperidinium perchlorate, 18h; transnitrosating studies; Rate constant;

Journal of Organic Chemistry, 1980 , vol. 45, # 24 p. 4931 - 4935 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 2470180 Find similar reactions

B: 55 mg

With sodium hydroxide in methanol

1 h; Heating;

Findlay; Radics

Canadian Journal of Chemistry, 1980 , vol. 58, # 6 p. 579 - 590 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in methanol; water

Heating;

Findlay; Radics

Canadian Journal of Chemistry, 1980 , vol. 58, # 6 p. 579 - 590 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 25275796 Find similar reactions

With hydrogenchloride; nitrogen

Hide Experimental Procedure

The Dow Chemical Company

Patent: US3959365 A1, 1976 ; Title/Abstract Full Text Show Details

2:EXAMPLE 2

EXAMPLE 2 The general procedure of Example 1 is followed, except that the 1-acetyl-2-cyanopiperidine is treated with (1) a nitrogen pressure of 500 psi instead of 200 psi, (2) twenty grams (ca. 0.45 moles) of carbon dioxide is used instead of 0.39 moles and (3) 15 ml. of six normal hydrochloric acid for 191/2 hours, instead of 13 ml. of 6N.HCl for 20 hours. The yields of lysine and pipecolic acid are 24 and 56percent respectively.

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Rx-ID: 5704982 Find similar reactions

With phosphorus; bromine

anschliessendes Erwaermen und Behandeln der Reaktionsloesung mit wss. Ba(OH)2;

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Lukes; Vesely

Collection of Czechoslovak Chemical Communications, 1959 , vol. 24, p. 2318,2321 Full Text Show Details

With water; platinum

T=90°C; Hydrogenation;

Rx-ID: 5705667 Find similar reactions

Fowden

Biochemical Journal, 1958 , vol. 70, p. 629,630 Full Text Show Details

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With hydrogenchloride

Einengen unter vermindertem Druck;

Rx-ID: 5704981 Find similar reactions

Hayakawa et al.

Nippon Kagaku Zasshi, 1953 , vol. 74, p. 826 Chem.Abstr., 1955 , p. 7566 Full Text Show Details

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Rx-ID: 5415357 Find similar reactions

Sorm

Collection of Czechoslovak Chemical Communications, 1948 , vol. 13, p. 57,68 Full Text Show Details

T=20°C; Electrolysis;

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Rx-ID: 5704983 Find similar reactions

Ost

Journal fuer Praktische Chemie (Leipzig), 1883 , vol. <2> 27, p. 293 Journal fuer Praktische Chemie (Leipzig), 1884 , vol. <2> 29, p. 61 Full Text Show Details

With P4; hydrogen iodide

T=160°C;

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Rx-ID: 5704984 Find similar reactions

Ost

Journal fuer Praktische Chemie (Leipzig), 1883 , vol. <2> 27, p. 293 Journal fuer Praktische Chemie (Leipzig), 1884 , vol. <2> 29, p. 61 Full Text Show Details

With P4; hydrogen iodide

T=160°C;

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Synthesize Find similar With hydrogen iodide

T=155 - 160°C;

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Rx-ID: 5704985 Find similar reactions

Ost

Journal fuer Praktische Chemie (Leipzig), 1883 , vol. <2> 27, p. 293 Journal fuer Praktische Chemie (Leipzig), 1884 , vol. <2> 29, p. 61 Full Text Show Details