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Citations (28)
References
1
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Rx-ID: 365781 Find similar reactions
With sodium dithionite; potassium carbonate; N,N'-dioctyl-4,4'bipyridinium in water; acetonitrile
T=35°C; 24 h;
Park, Kwanghee Koh; Oh, Chang Hun; Sim, Woo-Jeon
Journal of Organic Chemistry, 1995 , vol. 60, # 19 p. 6202 - 6204 Title/Abstract Full Text View citing articles Show Details
With hydrogenchloride; tin
Kurssanow
Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1906 , vol. 38, p. 1300 Chem. Zentralbl., 1907 , vol. 78, # I p. 1744 Full Text View citing articles Show Details
2
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Rx-ID: 968793 Find similar reactions
(i) NaN3, xylene, (ii) aq. HCl; Multistep reaction;
Bonnekessel,J.; Ruechardt,C.
Chemische Berichte, 1973 , vol. 106, p. 2890 - 2903 Full Text View citing articles Show Details
(i) NaN3, toluene, (ii) aq. HCl, toluene; Multistep reaction;
Carissimi; D'Ambrosio; Grumelli; Milla; Ravenna
Il Farmaco; edizione scientifica, 1966 , vol. 21, # 2 p. 155 - 171 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: aq. NH3
2: Br2 / methanol 3: KOH / bis-(2-hydroxy-ethyl) ether View Scheme
Kalir,A.; Pelah,K.
Israel Journal of Chemistry, 1967 , vol. 5, p. 223 - 229 Full Text View citing articles Show Details
3
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Rx-ID: 978885 Find similar reactions
Stage #1: With diphenyl phosphoryl azide; triethylamine in toluene
T=90°C; 2 h; Inert atmosphereReflux; Stage #2: With hydrogenchloride in water
Reflux;
Weinstein, Adam B.; Ellman, Jonathan A.
Organic Letters, 2016 , vol. 18, # 13 p. 3294 - 3297 Title/Abstract Full Text View citing articles Show Details
(i) aq. NaN3, ClCO2Et, Et3N, acetone, (ii) toluene, (iii) aq. HCl; Multistep reaction;
Palmere,R.M.; Conley,R.T.
Journal of Organic Chemistry, 1970 , vol. 35, p. 2703 - 2707 Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: SOCl2 / Heating 2: (i) NaN3, toluene, (ii) aq. HCl, toluene View Scheme
Carissimi; D'Ambrosio; Grumelli; Milla; Ravenna
Il Farmaco; edizione scientifica, 1966 , vol. 21, # 2 p. 155 - 171 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 4 steps
Kalir,A.; Pelah,K.
1: SOCl2 / benzene 2: aq. NH3
3: Br2 / methanol 4: KOH / bis-(2-hydroxy-ethyl) ether View Scheme
Israel Journal of Chemistry, 1967 , vol. 5, p. 223 - 229 Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: SOCl2 / dimethylformamide 2: (i) NaN3, xylene, (ii) aq. HCl View Scheme
Bonnekessel,J.; Ruechardt,C.
Chemische Berichte, 1973 , vol. 106, p. 2890 - 2903 Full Text View citing articles Show Details
4
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Rx-ID: 1032538 Find similar reactions
With potassium cyanide; sulfuric acid in anhydrous butyl ether
T=60 - 80°C;
Christol,H. et al.
Bulletin de la Societe Chimique de France, 1961 , p. 2319 - 2324 Full Text View citing articles Show Details
(i) NaN3, CF3CO2H, CHCl3, (ii) Raney-Ni, iPrOH; Multistep reaction;
Balderman,D.; Kalir,A.
Synthesis, 1978 , p. 24 - 26 Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: NaN3, CF3COOH / CHCl3 / 1.) 5 deg C, 2.) room temp., overnight 2: LiAlH4 / diethyl ether / 3 h View Scheme
Thurkauf, Andrew; Costa, Brian de; Yamaguchi, Shun-ichi; Mattson, Mariena V.; Jacobson, Arthur E.; et al.
Journal of Medicinal Chemistry, 1990 , vol. 33, # 5 p. 1452 - 1458 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: sodium azide; trifluoroacetic acid / dichloromethane / 1.25 h / -5 - 0 °C / Inert atmosphere 2: lithium aluminium tetrahydride / diethyl ether / 3 h / 20 °C / Inert atmosphere View Scheme
Tagad, Harichandra D.; Hamada, Yoshio; Nguyen, Jeffrey-Tri; Hidaka, Koushi; Hamada, Takashi; Sohma, Youhei; Kimura, Tooru; Kiso, Yoshiaki
Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 17 p. 5238 - 5246 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: sodium azide; trifluoroacetic acid / chloroform / 0 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere View Scheme
Sun, Shengguo; Wallach, Jason; Adejare, Adeboye
Medicinal Chemistry, 2014 , vol. 10, # 8 p. 843 - 852 Title/Abstract Full Text View citing articles Show Details
5
Synthesize Find similar With potassium hydroxide in diethylene glycol
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Rx-ID: 1143882 Find similar reactions
Kalir,A.; Pelah,K.
Israel Journal of Chemistry, 1967 , vol. 5, p. 223 - 229 Full Text View citing articles Show Details
6
Synthesize Find similar With lithium aluminium tetrahydride in tetrahydrofuran
Heating;
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Rx-ID: 1383884 Find similar reactions
Drefahl,G. et al.
Journal fuer Praktische Chemie (Leipzig), 1964 , vol. 23, p. 136 - 142 Full Text View citing articles Show Details
7
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Rx-ID: 1971107 Find similar reactions
99%
With hydrazine hydrate in ethanol
T=20°C; chemoselective reaction;
Udumula, Venkatareddy; Nazari, S. Hadi; Burt, Scott R.; Alfindee, Madher N.; Michaelis, David J.
ACS Catalysis, 2016 , vol. 6, # 7 p. 4423 - 4427 Title/Abstract Full Text View citing articles Show Details
75%
With lithium aluminium tetrahydride in tetrahydrofuran
T=0 - 20°C; 12 h; Inert atmosphere; Hide Experimental Procedure
Sun, Shengguo; Wallach, Jason; Adejare, Adeboye
Medicinal Chemistry, 2014 , vol. 10, # 8 p. 843 - 852 Title/Abstract Full Text View citing articles Show Details
Preparation of 1-(1-phenylcyclohexyl)amine
General procedure: The azide (5.0 g, 21 mmol) was dissolved in 20 ml dryTHF and the mixture was then added dropwise over 30 minto a stirred solution of lithium aluminum hydride (LAH, 2.4g, 63 mmol) in 40 ml dry THF at 0 °C under nitrogen. Uponcompletion of the addition, the reaction was allowed to recoverto room temperature. After 12 hours, the mixture wasplaced on ice and carefully quenched with water and a fewdrops of 2N aqueous KOH solution. The slurry was dilutedwith ether and gravity filtered and the salts washed withether. Ether (100 ml) was added and the organic phase extractedwith 2N HCl solution (3 x 20 ml). The acidic fractionswere pooled and adjusted to pH 10 with ammonia solution(or alternatively KOH) followed by extraction with ether(3 x 40 ml). The ethereal extracts were pooled, dried overanhydrous sodium sulfate and reduced under vacuum to givethe crude amine as a yellow oil. This oil was purified by columnchromatography using a mixture of CHCl3 and diethylether (9:1, v/v) as mobile phase to give 1-(4-fluorophenyl)cycloheptanamine 3 67%
With lithium aluminium tetrahydride in diethyl ether
T=20°C; 3 h; Inert atmosphere; Hide Experimental Procedure
Tagad, Harichandra D.; Hamada, Yoshio; Nguyen, Jeffrey-Tri; Hidaka, Koushi; Hamada, Takashi; Sohma, Youhei; Kimura, Tooru; Kiso, Yoshiaki
Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 17 p. 5238 - 5246 Title/Abstract Full Text View citing articles Show Details
5.2.6. 1-Phenylcyclohexylamine (8b)
General procedure: A solution of 1-phenylcyclopentylazide 7a (132 mg, 1.42 mmol) in diethyl ether (Et2O) (1 mL) was added dropwise to a suspension of lithium aluminum hydride (54 mg, 1.42 mmol) in Et2O (4 mL). The mixture was stirred at room temperature under nitrogen for 3 h, whereupon the reaction was quenched with 1 N NaOH (aq). The reaction mixture was then partitioned between Et2O (5 mL) and 1 N HCl (aq) (5 mL). The aqueous layer was collected and basified with 28percent NH4OH (aq) and extracted with CHCl3. The organic layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained crude product 8a (70.5 mg, 62percent) was used directly for next step without further purification.
38%
With Raney nickel in isopropyl alcohol
T=60 - 70°C;
Balderman, David; Kalir, Asher
1981 , vol. 60, p. 104 Title/Abstract Full Text Show Details
With lithium aluminium tetrahydride in diethyl ether
3 h; Yield given;
Thurkauf, Andrew; Costa, Brian de; Yamaguchi, Shun-ichi; Mattson, Mariena V.; Jacobson, Arthur E.; et al.
Journal of Medicinal Chemistry, 1990 , vol. 33, # 5 p. 1452 - 1458 Title/Abstract Full Text View citing articles Show Details
8
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Rx-ID: 7715439 Find similar reactions
1-Phenyl-cyclohexen, NaCN, Dibutylaether, H2SO4 <40grad>;
MADDOX; GODEFROI; PARCELL
Journal of medicinal chemistry, 1965 , vol. 8, p. 230 - 235 Title/Abstract Full Text View citing articles Show Details
1-Phenyl-cyclohexancarbonsaeure-amid, Br2, aq.KOH;
MADDOX; GODEFROI; PARCELL
Journal of medicinal chemistry, 1965 , vol. 8, p. 230 - 235 Title/Abstract Full Text View citing articles Show Details
1-Phenyl-cyclohexan-carbonsaeureamid, Br2, aq. KOH; (als Hydrochlorid isoliert);
MADDOX; GODEFROI; PARCELL
Journal of medicinal chemistry, 1965 , vol. 8, p. 230 - 235 Title/Abstract Full Text View citing articles Show Details
N-Methoxycarbonyl-1-phenylcyclohexylamin I, ethanol. KOH;
Tanabe Seiyaku Co.Ltd.
Patent: JP652662 , 1959 ; Chem.Abstr., 1963 , vol. 58, # 13842 Full Text Show Details
nach bek.Methode;
Brine; Williams; Boldt; Carroll
Journal of Heterocyclic Chemistry, 1979 , vol. 16, # 7 p. 1425 - 1429 Title/Abstract Full Text View citing articles Show Details
entspr. Literaturzitat 7;
1-Phenylcyclohexylamin, Tritium, PdO2;
Kalir et al.
European Journal of Medicinal Chemistry, 1978 , vol. 13, p. 17,18 Full Text Show Details
Kalir et al.
European Journal of Medicinal Chemistry, 1978 , vol. 13, p. 17,18 Full Text Show Details
PHARMACOPEIA, INC.
Patent: WO2004/33440 A1, 2004 ; Location in patent: Page 281 ; Title/Abstract Full Text Show Details
Schering Corporation and Pharmacopeia, Inc.
Patent: US2004/147559 A1, 2004 ; Location in patent: Page 153 ; Title/Abstract Full Text Show Details
Hide Experimental Procedure
Merck Sharp and Dohme Limited
Patent: US5627211 A1, 1997 ; Title/Abstract Full Text Show Details
5:1-(Bis-3,5-trifluoromethylbenzyoxy)-2-amino-2-phenylcyclohexane
EXAMPLE 5 1-(Bis-3,5-trifluoromethylbenzyoxy)-2-amino-2-phenylcyclohexane The title compound was prepared using an analogous procedure as outlined in Example 1 but using Bis-3,5-trifluoromethylbenzyl alcohol. 1 H NMR (360 MHz, DMSO) δ 1.40-1.52 (2H, m), 2.61-2.73 (2H, m), 2.78-2.84 (2H, m), 1.98-2.04 (1H, m), 2.06-2.09 (1H, m), 4.02 (1H, t, J=6.3 Hz), 4.50, 4.79 (2H, ABq, J=12.9 Hz), 7.33-7.43 (3H, m), 7.59-7.61 (2H, m), 7.85 (2H, s) and 7.96 (1H, s). The oxalate salt was recrystallized from ethanol/water mp 119°-122° C. Found: C, 53.96; H, 4.48; N, 2.70; C21 H21 F6 NO.C2 H2 O4.(0.25)H2 O; C, 53.96; H, 4.62; N, 2.73percent.
9
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Rx-ID: 21931900 Find similar reactions
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0.33 h 2: NaN3, CF3COOH / CHCl3 / 1.) 5 deg C, 2.) room temp., overnight 3: LiAlH4 / diethyl ether / 3 h View Scheme
Thurkauf, Andrew; Costa, Brian de; Yamaguchi, Shun-ichi; Mattson, Mariena V.; Jacobson, Arthur E.; et al.
Journal of Medicinal Chemistry, 1990 , vol. 33, # 5 p. 1452 - 1458 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 1.17 h / Cooling with ice; Reflux 1.2: 3 h / 0 - 20 °C 2.1: sodium azide; trifluoroacetic acid / dichloromethane / 1.25 h / -5 - 0 °C / Inert atmosphere 3.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 20 °C / Inert atmosphere View Scheme
Tagad, Harichandra D.; Hamada, Yoshio; Nguyen, Jeffrey-Tri; Hidaka, Koushi; Hamada, Takashi; Sohma, Youhei; Kimura, Tooru; Kiso, Yoshiaki
Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 17 p. 5238 - 5246 Title/Abstract Full Text View citing articles Show Details
10
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Rx-ID: 21932867 Find similar reactions
Thurkauf, Andrew; Costa, Brian de; Yamaguchi, Shun-ichi; Mattson, Mariena V.; Jacobson, Arthur E.; et al.
Journal of Medicinal Chemistry, 1990 , vol. 33, # 5 p. 1452 - 1458 Title/Abstract Full Text View citing articles Show Details
11
Synthesize Find similar Multi-step reaction with 2 steps 1: nitric acid / 100 - 110 °C / im geschlossenen Rohr 2: tin; hydrochloric acid View Scheme
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Rx-ID: 22125803 Find similar reactions
Kurssanow
Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1906 , vol. 38, p. 1300 Chem. Zentralbl., 1907 , vol. 78, # I p. 1744 Full Text View citing articles Show Details
12
Synthesize Find similar Multi-step reaction with 3 steps 1: aq. KOH / ethane-1,2-diol / Heating 2: SOCl2 / Heating 3: (i) NaN3, toluene, (ii) aq. HCl, toluene View Scheme
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Rx-ID: 22429836 Find similar reactions
Carissimi; D'Ambrosio; Grumelli; Milla; Ravenna
Il Farmaco; edizione scientifica, 1966 , vol. 21, # 2 p. 155 - 171 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 5 steps 1: KOH / bis-(2-hydroxy-ethyl) ether 2: SOCl2 / benzene 3: aq. NH3
4: Br2 / methanol 5: KOH / bis-(2-hydroxy-ethyl) ether View Scheme
Kalir,A.; Pelah,K.
Israel Journal of Chemistry, 1967 , vol. 5, p. 223 - 229 Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: KOH / bis-(2-hydroxy-ethyl) ether 2: SOCl2 / dimethylformamide 3: (i) NaN3, xylene, (ii) aq. HCl View Scheme
Bonnekessel,J.; Ruechardt,C.
Chemische Berichte, 1973 , vol. 106, p. 2890 - 2903 Full Text View citing articles Show Details
13
Synthesize Find similar Multi-step reaction with 2 steps 1: (i) silver fulminate, I2, Et2O, (ii) aq. HCl 2: LiAlH4 / tetrahydrofuran / Heating View Scheme
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Rx-ID: 22430997 Find similar reactions
Drefahl,G. et al.
Journal fuer Praktische Chemie (Leipzig), 1964 , vol. 23, p. 136 - 142 Full Text View citing articles Show Details
14
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15
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Rx-ID: 22441418 Find similar reactions
Kalir,A.; Pelah,K.
Israel Journal of Chemistry, 1967 , vol. 5, p. 223 - 229 Full Text View citing articles Show Details
Synthesize Find similar Multi-step reaction with 4 steps 1: KOtBu / 2-methyl-propan-2-ol 2: KOH / bis-(2-hydroxy-ethyl) ether 3: SOCl2 / dimethylformamide 4: (i) NaN3, xylene, (ii) aq. HCl View Scheme
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Rx-ID: 22749755 Find similar reactions
Bonnekessel,J.; Ruechardt,C.
Chemische Berichte, 1973 , vol. 106, p. 2890 - 2903 Full Text View citing articles Show Details
16
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Rx-ID: 24426157 Find similar reactions
With hydrogenchloride; triphenylphosphine in 1,4-dioxane; diethyl ether; acetonitrile
Hide Experimental Procedure
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Pfizer Inc
Patent: US6130217 A1, 2000 ; Title/Abstract Full Text Show Details
88:1-Phenylcyclohexylamine
The crude azide (18.0 g, <=96 mmol) was dissolved in dioxane (300 mL) with triphenylphosphine (40 g, 152 mmol) and the stirred solution was refluxed for 4 h. under N2 (g) before adding H2 O (9 mL, 0.5 mol). After about 46 h. further reflux, solvent was removed in vacuo at about 45-50° C. and residual moisture was removed by azeotropic distillations in vacuo with CH3 CN and Et2 O, respectively. The syrupy residue was dissolved in boiling Et2 O and chilled to about 0° C. for about 16 h. Precipitated Ph3 PO was removed by filtration, and 1M HCl in Et2 O (90 mL) was added dropwise at about 5° C. to the etherol filtrate to precipitate the desired 1-phenyl-cyclohexylamine as its HCl salt (12.7 g, LC-MS m/z 162 (MH+)) which was recrystallized from CHCl3 /i-Pr2 O before use.
17
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With hydrogen; palladium 10 on activated carbon in methanol
Hide Experimental Procedure
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Rx-ID: 24813277 Find similar reactions
ELI LILLY AND COMPANY
Patent: WO2006/49952 A1, 2006 ; Location in patent: Page/Page column 61-62 ; Title/Abstract Full Text Show Details
28:
Preparation 28; 1 -Phenyl-cyclohexylamine; Dissolve (l-phenyl-cyclohexyl)-carbamic acid benzyl ester (Preparation 27) (2.87 g, 9.26 mmol) in MeOH (100 mL). Exchange air with nitrogen for three times and then EPO <DP n="64"/>add Pd-C (0.5 g, 10percent). Exchange the nitrogen with H2 for three times. Stir the reaction mixture under H2 for over night then remove the Pd-C by filtration. Remove the solvent under reduced pressure to give 1.468 g (90percent) of the crude title compound as a colorless oil.
18
Synthesize Find similar Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 1.17 h / Cooling with ice; Reflux 1.2: 3 h / 0 - 20 °C 2.1: sodium azide; trifluoroacetic acid / dichloromethane / 1.25 h / -5 - 0 °C / Inert atmosphere 3.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 20 °C / Inert atmosphere View Scheme
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Rx-ID: 31541049 Find similar reactions
Tagad, Harichandra D.; Hamada, Yoshio; Nguyen, Jeffrey-Tri; Hidaka, Koushi; Hamada, Takashi; Sohma, Youhei; Kimura, Tooru; Kiso, Yoshiaki
Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 17 p. 5238 - 5246 Title/Abstract Full Text View citing articles Show Details
19
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With sodium hydroxide in methanol
7 h; Reflux;
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Rx-ID: 35902160 Find similar reactions
Miyoshi, Tetsuya; Matsuya, Syota; Tsugawa, Mikako; Sato, Shohei; Ueda, Masafumi; Miyata, Okiko
Organic Letters, 2013 , vol. 15, # 13 p. 3374 - 3377 Title/Abstract Full Text View citing articles Show Details
A
B
20
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With sodium dithionite; potassium carbonate; N,N'-dioctyl-4,4'bipyridinium in water; acetonitrile
T=35°C; 2 h; Yield given. Yields of byproduct given;
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Park, Kwanghee Koh; Oh, Chang Hun; Sim, Woo-Jeon
Journal of Organic Chemistry, 1995 , vol. 60, # 19 p. 6202 - 6204 Title/Abstract Full Text View citing articles Show Details
21
Synthesize Find similar With hydrogenchloride; hydrogen; palladium on activated charcoal in ethanol
T=50°C; P=2585.7 Torr; 24 h; Yield given;
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Rx-ID: 3620921 Find similar reactions
Baker; Little
Journal of Medicinal Chemistry, 1985 , vol. 28, # 1 p. 46 - 50 Title/Abstract Full Text View citing articles Show Details
22
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Rx-ID: 29350182 Find similar reactions
13%
Stage #1: in diethyl ether
T=20°C; 0.5 h; Stage #2: With titanium (IV) isopropoxide in diethyl ether
T=20°C; 24 h; Further stages;
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Tomashenko, Olesya A.; Rudenko, Andrei E.; Sokolov, Viktor V.; Tomashevskiy, Alexander A.; De Meijere, Armin
European Journal of Organic Chemistry, 2010 , # 8 p. 1574 - 1578 Title/Abstract Full Text View citing articles Show Details
23
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With hydrogenchloride in diethyl ether Hide Experimental Procedure
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Rx-ID: 40018320 Find similar reactions
Sun, Shengguo; Wallach, Jason; Adejare, Adeboye
Medicinal Chemistry, 2014 , vol. 10, # 8 p. 843 - 852 Title/Abstract Full Text View citing articles Show Details
General procedure: The HCl salt 4 was obtained by bubbling HCl gas into anethereal solution of the free base
24
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Multi-step reaction with 3 steps 1: sodium azide; trifluoroacetic acid / chloroform / 0 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 3: hydrogenchloride / diethyl ether View Scheme
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Rx-ID: 40018347 Find similar reactions
Sun, Shengguo; Wallach, Jason; Adejare, Adeboye
Medicinal Chemistry, 2014 , vol. 10, # 8 p. 843 - 852 Title/Abstract Full Text View citing articles Show Details
25
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Multi-step reaction with 2 steps
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Rx-ID: 40018348 Find similar reactions
Sun, Shengguo; Wallach, Jason; Adejare, Adeboye
1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 - 20 °C / |Inert atmosphere 2: hydrogenchloride / diethyl ether View Scheme
Medicinal Chemistry, 2014 , vol. 10, # 8 p. 843 - 852 Title/Abstract Full Text View citing articles Show Details
26
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Stage #1: With sodium hydroxide in water; butan-1-ol
T=0°C; Hofmann Rearrangement; 1 h; Stage #2: With sodium hypochlorite in water; butan-1-ol
T=20°C; 17 h; Stage #3: With hydrogenchloride in ethyl acetate
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Rx-ID: 45682031 Find similar reactions
Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young
Patent: KR2017/43091 A, 2017 ; Location in patent: Paragraph 0255; 0262-0264 ; Title/Abstract Full Text Show Details
Hide Experimental Procedure
6.3:Synthesis of 1-phenylcyclohexane-1-amine hydrochloride
In step 2 manufactured 1-phenylcyclohexane-1-carboxamide (1.090 g, 5.362 mmol) and sodium hydroxide (3.00 M solution in water, 5.004 mL, 15.013 mmol) Was dissolved in 1-butanol (30 mL) was stirred at 0 °C for 1 hour, and sodium hypochlorite (11.00percent, 5.080 g, 7.507 mmol), and the mixture was further stirred at room temperature for 17 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was dissolved in ethyl acetate, and hydrochloric acid (4 M solution, 2.011 mL, 8.043 mmol) was added and stirred. The precipitated solid was filtered, washed with ethyl acetate and dried to give the title compound (0.536 g, 47.2percent) as a white solid.