Reaxys
PubChem
eMolecules
Reactions (16)
Yield
Substances (5)
Conditions
Citations (21)
References
1
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Rx-ID: 2735991 Find similar reactions
73%
2
in diethyl ether; benzene
T=20°C;
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Katritzky, Alan R.; Najzarek, Zbigniew; Dega-Szafran, Zofia
Synthesis, 1989 , # 1 p. 66 - 69 Title/Abstract Full Text Show Details
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Rx-ID: 6458498 Find similar reactions
Union Carbide Chemicals and Plastics Technology Corporation
Patent: US5302767 A1, 1994 ; Title/Abstract Full Text Show Details
3:PCP Preparation with Air Atmosphere
EXAMPLE 3 PCP Preparation with Air Atmosphere 326 g of DMSO was heated to 85° C. in a 1 l baffled, glass resin kettle. 160 g of 50 weight percent aqueous sodium hydroxide was added, and the reactor contents were allowed to return to 85° C. 120 g of 50 weight percent aqueous Q-salt solution, as prepared in accordance with Example 1, was added over a period of 1 minute. The reactor contents were then maintained at 85° C. for a further 25 hours. Throughout this period, the reaction mixture was left exposed to the air. At the end of the reaction period, finely dispersed, off-white solids had formed. These were collected by filtration, washed with water, and then refluxed in 400 ml toluene for 60 minutes. The resulting solution was filtered while still hot to remove the undissolved polymer. The toluene was allowed to cool and the resulting crystals were recovered by filtration. A second crop of crystals was taken by stripping toluene, allowing the remaining solution to cool and recovering the resulting crystals by filtration. The resulting solids were washed with acetone and dried in an oven, yielding 15.3 g of PCP (51percent yield) as white crystals. 0.6 g (2.0percent yield) of polymer were recovered. 37%
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Union Carbide Chemicals and Plastics Technology Corporation
Patent: US5302767 A1, 1994 ; Title/Abstract Full Text Show Details
C.A:PCP Preparation with Nitrogen COMPARATIVE EXAMPLE A PCP Preparation with Nitrogen 326 g of DMSO was heated to 85° C. in a 1 liter (1) baffled, glass resin kettle. 160 g of 50 weight percent aqueous sodium hydroxide was added, and the reactor contents allowed to return to 85° C. 120 g of 50 weight percent aqueous Q-salt solution, as prepared in accordance with Example 1, was added over a period of 1 minutes. The reactor contents were then maintained at 85° C. for a further 25 hours. Throughout this period, a nitrogen atmosphere was maintained over the reaction mixture. At the end of the reaction period, finely dispersed, off-white solids had formed. These were collected by filtration, washed with water, and then refluxed in 400 milliliters (ml) toluene for 60 minutes. The resulting solution was filtered while still hot to remove the undissolved polymer. The toluene was allowed to cool and the resulting crystals were recovered by filtration. A second crop of crystals was taken by stripping toluene, allowing the remaining solution to cool and recovering the resulting crystals by filtration. The resulting solids were washed with acetone and dried in an oven, yielding 11.7 g of PCP (37percent yield) as white crystals. 3.0 g (9.6percent yield) of polymer were recovered. 25.8%
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Union Carbide Chemicals and Plastics Technology Corporation
Patent: US5302767 A1, 1994 ; Title/Abstract Full Text Show Details
4:PCP Preparation with Air Sparge
EXAMPLE 4 PCP Preparation with Air Sparge 3848 g of DMSO were heated to 85° C. in a 12 l stirred tank reactor. 960 g sodium hydroxide pellets, 810 g of distilled water and 1600 g of 42.3 weight percent aqueous Q-salt solution, prepared in accordance with Example 1, were added. The reactor contents were then maintained at 85° C. for a further 4 hours. Throughout this period, the reaction mixture was sparged with air at a flow rate of 400 ml per minute. 91.2 g of PCP (25.8percent yield) and 3.3 g (0.9percent yield) of polymer were obtained following the recovery method described in Example A. Hide Details 1.6%
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Union Carbide Chemicals and Plastics Technology Corporation
Patent: US5302767 A1, 1994 ; Title/Abstract Full Text Show Details
5:PCP Preparation with Oxygen Sparge
EXAMPLE 5 PCP Preparation with Oxygen Sparge 42.6 kilograms (kg) of DMSO were heated to 85° C. in a 30 gallon stirred tank reactor. 21.3 kg of 50 weight percent aqueous sodium hydroxide and 15.9 kg of 50 weight percent aqueous Q-salt solution, prepared in accordance with Example 1, were added. The reactor contents were then maintained at 85° C. for a further 4 hours. Throughout this period, the reaction mixture was sparged with 2 mol percent oxygen in nitrogen mixture at a flow rate of 2 l per minute. 1347 g of solids were filtered from the reaction mixture. 150.5 g of these solids were taken for PCP recovery, following the method described in Example A. 125.2 g of PCP (28percent yield) and 7 g (1.6percent yield) of polymer were obtained.
Maddox,V.H. et al.
J. Med. Chem., 1965 , vol. 8, p. 230 - 235 Title/Abstract Full Text View citing articles Show Details
Parke; Davis and Co.
Patent: US3097136 , 1960 ; Chem.Abstr., 1963 , vol. 59, # 13881 Full Text Show Details
Mousseron et al.
Chimica Therapeutica, 1966 , vol. 1, p. 284,286 Full Text Show Details
Sokolovsky; Hordeckai
Patent: DE2339342 , 1974 ; Chem.Abstr., vol. 80, # 132908 Full Text Show Details
Parke; Davis
Patent: US3192219 , 1965 ; Chem.Abstr., 1965 , vol. 63, # 9921f Full Text Show Details
Welvart
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1960 , vol. 250, p. 1870,1871 Full Text Show Details
Kalir et al.
European Journal of Medicinal Chemistry, 1978 , vol. 13, p. 17,18 Full Text Show Details
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University of Pittsburgh
Patent: US5132313 A1, 1992 ; Title/Abstract Full Text Show Details
Compounds 3 and 4
Compounds 3 and 4 A solution of 150 mg (0.81 mmol) of compound 1 or 2 in 5.6 mL of dry ethanol was stirred with 3.8 mg of PtO2 under hydrogen (1 atm) at room temperature for 1 h. Filtration and evaporation gave the compound 3 or 4 in quantitative yield. Rf =0.34 (40percent EtOAc in hexane, silica TLC saturated with NH3); IR (CHCl3) ν 3358, 3281, 3013, 2917, 2847, 1595, 1468, 1451, 1437, 747, 718 cm-1; 1
H NMR (CDCl3, 300 MHz) δ 7.35-7.16 (4H, m), 2.94 (1H, dd, J1 =7.1 Hz, J2 =15.5 Hz) 2.65 (1H, dd, J1 =7.7 Hz, J2 =15.5 Hz), 2.21-2.08 (1H, m), 1.94-1.30 (10H, m); C NMR (CDCl3, 125.76 MHz) δ 151.35, 141.67, 126.92, 126.49, 125.46, 121.43, 61.73, 48.72, 35.778, 34.77, 26.42, 22.46, 21.96;
13
MS (70 eV), m/z 187 (M+), 144, 130, 115, 91, 77; HRMS calcd. for C13 H17 N 187.1355, found 187.1355.
3
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Rx-ID: 9932094 Find similar reactions
80%
Stage #1: piperidine; cyclohexanone With 1H-(1,2,3)triazole in toluene
T=108 - 114°C; Stage #2: Bromure de phenyl magnesium in tetrahydrofuran; toluene
T=24°C; Bruylants reaction; 1.5 h;
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Prashad, Mahavir; Liu, Yugang; Har, Denis; Repic, Oljan; Blacklock, Thomas J.
Tetrahedron Letters, 2005 , vol. 46, # 33 p. 5455 - 5458 Title/Abstract Full Text View citing articles Show Details
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4
Synthesize Find similar Multi-step reaction with 2 steps 1: 50 percent / benzene / 2 h / Heating 2: 73 percent / diethyl ether; benzene / 20 °C View Scheme
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Rx-ID: 20377347 Find similar reactions
Katritzky, Alan R.; Najzarek, Zbigniew; Dega-Szafran, Zofia
Synthesis, 1989 , # 1 p. 66 - 69 Title/Abstract Full Text Show Details
5
Synthesize Find similar Multi-step reaction with 2 steps 1: 50 percent / benzene / 2 h / Heating 2: 73 percent / diethyl ether; benzene / 20 °C View Scheme
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Rx-ID: 20390522 Find similar reactions
Katritzky, Alan R.; Najzarek, Zbigniew; Dega-Szafran, Zofia
Synthesis, 1989 , # 1 p. 66 - 69 Title/Abstract Full Text Show Details
6
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Rx-ID: 28499295 Find similar reactions
58%
Stage #1: bromobenzene With iodine; magnesium in tetrahydrofuran; diethyl ether
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Ahmadi, Abbas; Khalili, Mohsen; Abbassi, Sara; Javadi, Mozhdeh; Mahmoudi, Ali; Hajikhani, Ramin
Arzneimittel-Forschung/Drug Research, 2009 , vol. 59, # 4 p. 202 - 206 Title/Abstract Full Text View citing articles Show Details
Stage #2: 1-piperidin-1-ylcyclohexanecarbonitrile in tetrahydrofuran; diethyl ether
Reflux;
58%
Stage #1: bromobenzene With iodine; magnesium in tetrahydrofuran
Ahmadi, Abbas; Solati, Jalal; Hajikhani, Ramin; Pakzad, Sara
Asian Journal of Chemistry, 2011 , vol. 23, # 12 p. 5429 - 5432 Title/Abstract Full Text View citing articles Show Details
Stage #2: 1-piperidin-1-ylcyclohexanecarbonitrile in tetrahydrofuran
Stage #1: bromobenzene With iodine; magnesium in tetrahydrofuran
Ahmadi, Abbas; Khalili, Mohsen; Mihandoust, Farnaz; Barghi, Leila
Arzneimittel-Forschung/Drug Research, 2010 , vol. 60, # 1 p. 30 - 35 Title/Abstract Full Text View citing articles Show Details
Stage #2: 1-piperidin-1-ylcyclohexanecarbonitrile
Hide Details Stage #1: bromobenzene With iodine; magnesium in tetrahydrofuran
Ahmadi, Abbas; Solati, Jalal; Hajikhani, Ramin; Onagh, Masoud; Javadi, Mojdeh
Arzneimittel-Forschung/Drug Research, 2010 , vol. 60, # 8 p. 492 - 496 Title/Abstract Full Text View citing articles Show Details
Stage #2: 1-piperidin-1-ylcyclohexanecarbonitrile
Stage #1: bromobenzene With iodine; magnesium in diethyl ether Reflux; Stage #2: 1-piperidin-1-ylcyclohexanecarbonitrile in diethyl ether; toluene
Reflux;
Ahmadi; Kermani; Naderi; Hajikhani; Rezaee; Javadi; Niknafs
Current Medicinal Chemistry, 2012 , vol. 19, # 5 p. 763 - 769 Title/Abstract Full Text View citing articles Show Details
7
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Rx-ID: 30653970 Find similar reactions
Multi-step reaction with 2 steps 1: hydrogenchloride 2: iodine; magnesium / tetrahydrofuran View Scheme
Ahmadi, Abbas; Solati, Jalal; Hajikhani, Ramin; Onagh, Masoud; Javadi, Mojdeh
Arzneimittel-Forschung/Drug Research, 2010 , vol. 60, # 8 p. 492 - 496 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: hydrogenchloride View Scheme
Ahmadi, Abbas; Solati, Jalal; Hajikhani, Ramin; Onagh, Masoud; Javadi, Mojdeh
Arzneimittel-Forschung/Drug Research, 2010 , vol. 60, # 8 p. 492 - 496 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps
Ahmadi; Kermani; Naderi; Hajikhani; Rezaee; Javadi; Niknafs
Current Medicinal Chemistry, 2012 , vol. 19, # 5 p. 763 - 769
1.1: sodium hydrogensulfite 2.1: iodine; magnesium / diethyl ether / Reflux 2.2: Reflux View Scheme
8
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Rx-ID: 30653972 Find similar reactions
58%
9
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Ahmadi, Abbas; Solati, Jalal; Hajikhani, Ramin; Onagh, Masoud; Javadi, Mojdeh
Arzneimittel-Forschung/Drug Research, 2010 , vol. 60, # 8 p. 492 - 496 Title/Abstract Full Text View citing articles Show Details
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Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 30653974 Find similar reactions
Multi-step reaction with 2 steps 1: hydrogenchloride 2: iodine; magnesium / tetrahydrofuran View Scheme
Ahmadi, Abbas; Solati, Jalal; Hajikhani, Ramin; Onagh, Masoud; Javadi, Mojdeh
Arzneimittel-Forschung/Drug Research, 2010 , vol. 60, # 8 p. 492 - 496 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: hydrogenchloride View Scheme
Ahmadi, Abbas; Solati, Jalal; Hajikhani, Ramin; Onagh, Masoud; Javadi, Mojdeh
Arzneimittel-Forschung/Drug Research, 2010 , vol. 60, # 8 p. 492 - 496 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1.1: sodium hydrogensulfite 2.1: iodine; magnesium / diethyl ether / Reflux 2.2: Reflux View Scheme
Ahmadi; Kermani; Naderi; Hajikhani; Rezaee; Javadi; Niknafs
Current Medicinal Chemistry, 2012 , vol. 19, # 5 p. 763 - 769 Title/Abstract Full Text View citing articles Show Details
10
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Rx-ID: 33447105 Find similar reactions
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Multi-step reaction with 2 steps 1: hydrochlorid acid 2: iodine; magnesium / tetrahydrofuran View Scheme
Ahmadi, Abbas; Solati, Jalal; Hajikhani, Ramin; Pakzad, Sara
Asian Journal of Chemistry, 2011 , vol. 23, # 12 p. 5429 - 5432 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1.1: NaHS03
2.1: iodine / diethyl ether 2.2: |Reflux View Scheme
Ahmadi, Abbas; Khalili, Mohsen; Barzin, Mahnaz; Pooladi, Mohsen; Bakhtiari, Fatemeh; Barjeste, Maede; Nahri-Niknafs, Babak
Monatshefte fur Chemie, 2016 , vol. 147, # 2 p. 457 - 464 Title/Abstract Full Text View citing articles Show Details
11
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Rx-ID: 41841458 Find similar reactions
Stage #1: bromobenzene; magnesium With iodine in diethyl ether
Bruylants Amination; Stage #2: 1piperidinocyclohexylcarbonitrile in diethyl ether; toluene
Bruylants Amination; Reflux; Hide Experimental Procedure
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Ahmadi, Abbas; Khalili, Mohsen; Barzin, Mahnaz; Pooladi, Mohsen; Bakhtiari, Fatemeh; Barjeste, Maede; Nahri-Niknafs, Babak
Monatshefte fur Chemie, 2016 , vol. 147, # 2 p. 457 - 464 Title/Abstract Full Text View citing articles Show Details
Preparation of compounds 9a–9k
General procedure: A solution of 0.0203 mol nitrile intermediates 1–6 in diethylether and toluene (1:1) were added to phenyl or2-thiophene magnesium bromide reagents (7 and 8, preparedfrom refluxing of 0.0503 mol bromobenzene or2-bromothiophene and 0.505 g of Mg in 100 cm3 of dryether). These mixtures were refluxed for additional hours(monitoring by TLC) and subsequently dipped into thesolution of ice-NH4Cl and NH4OH. The organic layerswere decanted and washed. The bases were acidified with10 percent H2SO4, basified with 10 percent NaOH, neutralized bywashing with water, extracted with ether, dried, and concentrated.The products were obtained as solids or viscousliquid compounds which for purification were passedthrough a silica gel column using ethyl acetate/n-hexane(95:5) as the eluent to yield 9a–9k.
12
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Rx-ID: 6432171 Find similar reactions
Phencyclidin, PdO/T2;
Kalir et al.
Journal of Labelled Compounds and Radiopharmaceuticals, 1977 , vol. 13, p. 445,446,447 Full Text View citing articles Show Details
Tetrahydropyridin 5, Pd/C, T2;
Kalir et al.
Journal of Labelled Compounds and Radiopharmaceuticals, 1977 , vol. 13, p. 445,446,447 Full Text View citing articles Show Details
13
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Rx-ID: 1756823 Find similar reactions
Yield given. Multistep reaction;
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Masumoto; Takeuchi; Ohta; Hirobe
Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 7 p. 1788 - 1794 Title/Abstract Full Text View citing articles Show Details
14
Synthesize Find similar aus Phenyl-d(5)Magnesiumbromid, 1-Piperidinocyclohexancarbonitril;
Rx-ID: 6863288 Find similar reactions
Fentiman; Foltz
Journal of Labelled Compounds and Radiopharmaceuticals, 1976 , vol. 12, p. 69,74 Full Text Show Details
15
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Rx-ID: 38526024 Find similar reactions
Multi-step reaction with 2 steps 1: sodium hydrogensulfite 2: iodine; magnesium / diethyl ether View Scheme
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Ahmadi, Abbas; Khalili, Mohsen; Hajikhani, Ramin; Naserbakht, Moslem
Pharmacology Biochemistry and Behavior, 2011 , vol. 98, # 2 p. 227 - 233 Title/Abstract Full Text View citing articles Show Details
16
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Rx-ID: 38526025 Find similar reactions
Stage #1: bromobenzene With iodine; magnesium in diethyl ether
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Ahmadi, Abbas; Khalili, Mohsen; Hajikhani, Ramin; Naserbakht, Moslem
Pharmacology Biochemistry and Behavior, 2011 , vol. 98, # 2 p. 227 - 233 Title/Abstract Full Text View citing articles Show Details
Stage #2: 1-piperidin-1-ylcyclohexanecarbonitrile in tetrahydrofuran; diethyl ether
Stage #3: With hydrogenchloride in diethyl ether; water; isopropyl alcohol
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1-[1-phenylcyclohexyl] piperidine (PCP) (I)
This compound was prepared in a 58percent yield based on a publishedmethod (Maddox et al., 1965) from adding a solution of 1-piperidinocyclohexanecarbonitrile (1) in an organic solvent to arefluxing solution of phenyl magnesium bromide (prepared from 79 gbromobenzene and 12.3 g of Mg in 200 ml of dry ether). Thehydrochloride salt of I(m.p. 233–234 °C)wasprepared using 2-propanoland HCl, and it was recrystallized from 2propanol.