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Chemical Structure| 20439-47-8 Chemical Structure| 20439-47-8
Chemical Structure| 20439-47-8

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Product Details of (1R,2R)-Cyclohexane-1,2-diamine

CAS No. :20439-47-8
Formula : C6H14N2
M.W : 114.19
SMILES Code : N[C@H]1[C@H](N)CCCC1
MDL No. :MFCD00062985
InChI Key :SSJXIUAHEKJCMH-PHDIDXHHSA-N
Pubchem ID :43806

Safety of (1R,2R)-Cyclohexane-1,2-diamine

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H303-H314-H335
Precautionary Statements:P210-P261-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P312-P363-P370+P378-P403+P233-P403+P235-P405-P501
Class:8
UN#:2735
Packing Group:

Application In Synthesis of (1R,2R)-Cyclohexane-1,2-diamine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 20439-47-8 ]

[ 20439-47-8 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 33985-71-6 ]
  • [ 20439-47-8 ]
  • (1R,2R)-N,N'-Bis-[1-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-meth-(E)-ylidene]-cyclohexane-1,2-diamine [ No CAS ]
  • 2
  • [ 33985-71-6 ]
  • [ 20439-47-8 ]
  • (R,R)-N,N'-bis<(2,3,6,7-tetrahydro-1H,5H-benzo<ij>quinolizin-9-yl)methylene>-1,2-cyclohexanediamine [ No CAS ]
  • 3
  • [ 37942-07-7 ]
  • [ 20439-47-8 ]
  • [ 151433-25-9 ]
YieldReaction ConditionsOperation in experiment
Heating / reflux; Chiral ligands were prepared by refluxing 1 ,2-cyclohexyldiamines {R,R and S1S) with 2,4 di-.erf-butyl salicylaldehyde
In ethanol; for 12h;Reflux; 1.14 g of (R,R)-1,2-cyclohexanediamine was dissolved in 20 mL of ethanol.4.7 g of 3,5-di-tert-butylsalicylaldehyde in 30 mL of ethanol solution was slowly added dropwise thereto.The resulting mixed solution was refluxed for 12 h.Obtaining a reaction mixture; removing the reaction solvent by filtration,The obtained reaction product ethanol was recrystallized to obtain a Schiff base ligand.The present invention performs elemental analysis on the obtained Schiff base compound,Obtaining the content of each atom therein,The results are as follows: Elem.Anal. (%): Calcd. C 79.07; H 9.95; N5.12.Found: C 78.71; H 9.85; N 4.77. this means,The Schiff base ligand obtained in this embodiment has the structure of formula II,Wherein Y is ((R,R)-1,2-cyclohexanediamine) and R is a tert-butyl group.
General procedure: In a round bottomed flask filled with argon, (1R,2R)-trans-1,2-diaminocyclohexane (R,R-DACH) (1 equiv.) and potassium carbonate (0.9 equiv.) were dissolved in 3mL of distilled water and heated for 30min at 80-85C. The exact amounts are given below. Subsequently, a solution of aldehyde (2 equiv.) in 45mL of ethanol was added dropwise and the reaction mixture was stirred for 3h. The solution turned yellow. After this time, ethanol was evaporated and 10mL of distilled water was added. Water solution was extracted with dichloromethane 3 times with 30mL of the solvent. The combined extracts were washed with brine and dried with anhydrous Na2SO4. After filtration of the drying agent, solution was evaporated to dryness. The resulting salens were subsequently reduced without purification. The resulting salens were dissolved in methanol (300mL or more if it was necessary for complete dissolution). To the salen solution, sodium borohydride (4 equiv.) was added in portions at room temperature. After addition of NaBH4, the reaction mixture was stirred for 3h and then 30mL of water was added and stirred for 15min. The alcohol was evaporated under vacuum and the water residue was extracted with DCM three times for 30mL. Organic phase was dried with Na2SO4 and after removing of the desiccant, the solvent was evaporated.
  • 4
  • [ 20439-47-8 ]
  • [ 100-52-7 ]
  • [ 65838-10-0 ]
YieldReaction ConditionsOperation in experiment
93% Synthesis of (lR,2R)-N,N'-dibenzylcyclohexane-l ,2-diamine; Benzaldehyde (4.65 g, 43.8 mmol) was added to a solution of (R,2R)-,2- diaminocyclohexane (2.50 g, 21.9 mmol) in methanol (13 ml). The reaction mixture was stirred at 700C for 6 h. Then NaBH4 (2.00 g, 52.7 mmol) was added in small portions at 700C during 30 minutes. After stirring for 3.5 hours at room temperature, the solvent was evaporated. The residue was taken up in dichloromethane and extracted with an aqueous solution of HCl (IN), the aqueous phase was separated, then NaOH (10% aqueous solution) was added to this aqueous phase to reach a pH of 10. Extraction with diethylether (3x), drying (Na2SO4) and concentrating gave 6.02 g (93%) of the desired diamine. 1H-NMR: 7.35-7.24 (m, 8 H); 7.24-7.16 (m, 2 H); 3.78 (d, J = 13.3, 2 H); 3.57 (d, J = 13.3, 2 H); 2.29-2.14 (m, 4 H); 2.02 (d, J = 13.3, 2 H); 1.68-1.57 (m, 2 H); 1.18-1.08 (m, 2 H); 1.06-0.92 (m, 2 H). <n="26"/>13C-NMR: 141.58 (s); 127.96 (d); 127.69 (d); 126.31 (d); 126.28 (d); 60.17 (d); 49.92 (t); 30.65 (t); 24.51 (t).
Benzaldehyde (12.72 g, 120 mmol) was added dropwise over a period of 2 minutes to a solution of (R,R)-cyclohexane-1,2-diamine (6.84 g, 60 mmol) in 100 mL of anhydrous MeOH at refluxing temperature. After stirring for 30 min, the solution was allowed to cool to room temperature and NaBH3CN (4.8 g, 126 mmol) was added in portions. After the vigorous effervescence subsided down, the mixture was brought to refluxing and stirred for 20 min. The reaction was quenched by water and extracted with dichloromethane. The organic phase was dried and concentrated to give 16.95 g of crude product (yield 96%) which was used in the next step reaction without further purification.
  • 5
  • [ 20439-47-8 ]
  • [ 7310-97-6 ]
  • [ 459166-16-6 ]
  • 6
  • [ 7044-92-0 ]
  • [ 20439-47-8 ]
  • (2R,3R,12R,13R,22R,23R)-1,4,11,14,21,24-hexaaza-(7,8',17,18',27,28')-hexamethyl-(2,3:12,13:22,23)-tributano-(6,9:16,19:26,29)-trietheno-(2H,3H,12H,13H,22H,23H)-hexahydro-(30)-annulene [ No CAS ]
  • 8
  • [ 37942-07-7 ]
  • [ 20439-47-8 ]
  • [ 360784-94-7 ]
  • [ 135616-40-9 ]
  • C38H38N2O2 [ No CAS ]
  • [ 886055-61-4 ]
  • 9
  • [ 3328-69-6 ]
  • [ 20439-47-8 ]
  • [ 656811-78-8 ]
  • 10
  • [ 7089-68-1 ]
  • [ 20439-47-8 ]
  • RR-N,N'-bis(phenanthrolin-2-yl)-1,2-cyclohexanediamine [ No CAS ]
  • 11
  • [ 20439-47-8 ]
  • [ 100-39-0 ]
  • [ 65838-10-0 ]
  • 12
  • [ 20439-47-8 ]
  • [ 100-39-0 ]
  • [ 65838-10-0 ]
  • [ 849819-90-5 ]
  • 13
  • [ 20439-47-8 ]
  • [ 34595-26-1 ]
  • (1R,2R)-N1,N2-bis(2-(piperidin-1-yl)benzylidene)cyclohexane-1,2-diamine [ No CAS ]
  • 16
  • [ 652-12-0 ]
  • [ 20439-47-8 ]
  • [ 23165-29-9 ]
  • [ 1012051-77-2 ]
  • 17
  • [ 67-56-1 ]
  • [ 3328-69-6 ]
  • [ 20439-47-8 ]
  • copper(II) perchlorate [ No CAS ]
  • [Cu(C6H10N2)(C6H3(O)(CH)2)(CH3OH)]2(2+)*2ClO4(1-)*2CH3OH=[Cu(C6H10N2)(C6H3(O)(CH)2)(CH3OH)]2(ClO4)2*2CH3OH [ No CAS ]
  • 18
  • [ 55589-47-4 ]
  • [ 20439-47-8 ]
  • [ 1293966-07-0 ]
  • 20
  • [ 20439-47-8 ]
  • [ 70049-46-6 ]
  • [ 1353892-00-8 ]
YieldReaction ConditionsOperation in experiment
77% With sodium t-butanolate;2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); In alpha,alpha,alpha-trifluorotoluene; at 120℃; for 0.166667h;Microwave irradiation; H,4CL6MEOQUIN-BAM. A 2-5 mL muW vial was charged with (R,R)-diaminocyclohexane (125.2 mg, 1.096 mmol), <strong>[70049-46-6]2,4-dichloro-<strong>[70049-46-6]6-methoxyquinoline</strong></strong> (500 mg, 2.190 mmol), Pd(dba)2 (12.6 mg, 22.0 mumol), rac-BINAP (13.6 mg, 22.0 mumol), and sodium tert-butoxide (316.2 mg, 3.290 mmol). See Wagaw et al., 1997, which is incorporated herein by reference. Trifluoromethylbenzene (3.8 mL) was added and the resulting suspension was heated at 120° C. and stirred in the microwave for 10 min. The reaction mixture was triturated with CH2Cl2 and filtered. The filtrate was concentrated and purified by column chromatography (10-20percent ethyl acetate in hexanes) to provide a yellow solid (420.3 mg, 77percent) that was pure by 1H NMR; [alpha]D20 +610 (c 0.18, CHCl3); Rf=0.18 (20percent EtOAc/hexanes); IR (film) 3218, 2925, 1605, 1495 cm-1; 1H NMR (600 MHz, CDCl3, 325 K) delta 7.64 (d, J=9.0 Hz, 2H), 7.30 (d, J=3.0 Hz, 2H), 7.25 (dd, J=9.0, 3.0 Hz, 2H), 6.38 (br s, 2H), 5.72 (br s, 2H), 4.05-3.90 (m, 2H), 3.91 (s, 6H), 2.39-2.25 (m, 2H), 1.90-1.80 (m, 2H), 1.55-1.35 (m, 4H); 13C NMR (150 MHz, CDCl3, 325 K) ppm 155.5, 155.4, 144.0, 141.4, 127.6, 121.9, 121.8, 111.8, 103.7, 56.1, 55.6, 33.0, 24.9; HRMS (ESI): Exact mass calcd for C26H27Cl2N4O2 [M+H]+ 497.1511. found 497.1500.
  • 21
  • [ 32608-29-0 ]
  • [ 20439-47-8 ]
  • [ 1370730-92-9 ]
YieldReaction ConditionsOperation in experiment
62% With sodium t-butanolate;2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); In toluene; at 70℃; for 3.5h; 4Cl8MeOQuinBAM. A 100 mL round bottom flask was charged with Pd(dba)2 (25.2 mg, 43.8 mumol), rac-BINAP (27.3 mg, 43.8 mumol), sodium tert-butoxide (632.0 mg, 6.576 mmol), (R,R)-diaminocyclohexane (250.3 mg, 2.192 mmol), and the quinoline (1.0000 g, 4.385 mmol).1 Toluene (22 mL) was added, and the reaction mixture was heated at 70 C. and stirred for 3.5 h. The reaction was cooled to room temperature, diluted with CH2Cl2, and filtered through celite. The filtrate was concentrated and purified by column chromatography (25-50% ethyl acetate in hexanes) to provide a yellow solid (642.6 mg, 62%). [alpha]D20 +530 (c 0.16, CHCl3); Rf=0.31 (50% EtOAc/hexanes); IR (film) 3240, 2933, 1607, 1545 cm-1; 1H NMR (400 MHz, CDCl3) delta 7.54 (dd, J=8.4, 0.8 Hz, 2H), 7.17 (dd, J=7.6, 0.8 Hz, 2H), 7.01 (dd, J=7.6, 0.8 Hz, 2H), 6.59 (s, 2H), 6.38 (br s, 2H), 4.15-3.95 (m, 2H), 4.04 (s, 6H), 2.45-2.30 (m, 2H), 1.85-1.70 (m, 2H), 1.50-1.30 (m, 4H); 13C NMR (150 MHz, CDCl3) ppm 155.9, 153.2, 142.1, 140.0, 122.2, 121.9, 116.2, 112.7, 109.8, 56.6, 56.2, 32.5, 24.7; HRMS (ESI): Exact mass calcd for C26H27Cl2N4O2 [M+H]+ 497.1511. found 497.1521. 1 Adapted from Wagaw, S.; Rennels, R.; Buchwald, S. J Am. Chem. Soc. 1997, 119, 8451-8458.
  • 22
  • [ 5779-93-1 ]
  • [ 20439-47-8 ]
  • C24H30N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With amberlyst 15; In toluene; for 12h;Molecular sieve; Inert atmosphere; Reflux; General procedure: Chiral bisformamides 1a-j were prepared as previously reported.11 (1R,2R)-1,2-Cyclohexanediamine (10 mmol), aldehyde (25 mmol), MS 4 A (4 g) and amberlyst 15 (0.2 g) in toluene (120 mL) were refluxed for 12 h, and the reaction mixture was cooled to room temperature. After the mixture was filtered, the solvent was concentrated and the residue was recrystallized from hexane to afford the corresponding imine.
  • 23
  • [ 28170-07-2 ]
  • [ 20439-47-8 ]
  • [ 142350-85-4 ]
  • 24
  • [ 20439-47-8 ]
  • [ 50606-58-1 ]
  • [ 76-05-1 ]
  • (1R,2R)-N1-(1-benzylpiperidin-3-yl)cyclohexane-1,2-diamine trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% l-Benzyl-3-piperidone hydrochloride monohydrate (5.93 g, 26.3 mmol) was partitioned between a saturated aqueous NaHCC solution (30ml) and (¾(¾ (50 mL). The organic layer was separated and dried over a2S04 and filtered. The filtrated was collected and (lR,2R)-cyclohexane-l,2-diamine (3 g, 26.3 mmol) was added followed by sodium triacetoxy borohydride (8.35 g, 39.4 mmol). The reaction was stirred at rt overnight. After this time, the reaction was quenched with water (2ml). The resulting solution was washed with saturated aqueous NaHCC (50 ml) and saturated NaCl (50 ml). The organic layer was dried over MgS04, filtered and concentrated. The resulting residue was purified by RP Prep-HPLC. The desired fractions containing the product were concentrated to give the product, (lR,2R)- l-(l-benzylpiperidin-3-yl)cyclohexane- 1,2-diamine (3.01 g, 10.47 mmol, 40 % yield) as a trifluoroacetate salt and as a white solid. ¾ NMR (500 MHz, MeOH-d3) delta ppm 7.54-7.36 (m, 5H), 4.27-3.99 (m, 2H), 3.24 -2.94 (m, 3H), 2.69 (d, J=9.90 Hz, 2H), 2.46-2.27 (m, 1H); 2.25-2.02 (m, 2H); 2.03-1.83 (m, 2H); 1.83-1.62 (m, 4H); 1.47-1.19 (m, 4H); 1.05 (d, J=l 1.55 Hz, 1H). 13C NMR (126 MHz, MeOH-d3) 5 ppm 132.27, 130.75, 130.25, 62.31, 58.81, 56.46, 53.57, 32.76, 31.33, 25.99, 25.73, 25.40
  • 26
  • [ 19832-98-5 ]
  • [ 20439-47-8 ]
  • (1R,2R)-N<SUP>1</SUP>,N<SUP>2</SUP>-bis(5-methylnaphthalen-1-yl)cyclohexane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With 5%-palladium/activated carbon; at 150℃; for 24h;Inert atmosphere; Sealed tube; General procedure: In a pres-sure tube were successively added under inert atmosphere, 1eq ofdiamine (2 mmol, 0.23 g), 3eq of -tetralone (6 mmol, 0.9 g) and2.5 mol% of Pd/C (5%) (0.05 mmol, 107 mg). Then, the tube wassealed and placed in preheated oil bath (T = 150C). After 24 h ofstirring at 800 rpm the crude was cooling down and diluted in amixture (50/50) of CH2Cl2and CH3OH then filtered off on Milli-pore filter (Durapore filter 0.01 m). The solvents were removedunder vacuum and the crude material was purified by flash col-umn chromatography on silica gel (Eluent cyclohexane (500 mL),then cyclohexane/ethyl acetate 90:10)
  • 27
  • [ 34374-88-4 ]
  • [ 20439-47-8 ]
  • C27H42N6O3 [ No CAS ]
  • C27H42N6O3 [ No CAS ]
  • 28
  • [ 34374-88-4 ]
  • [ 20439-47-8 ]
  • C36H42N6O6 [ No CAS ]
  • 29
  • [ 32596-43-3 ]
  • [ 20439-47-8 ]
  • (R,R)-[ClC6H2(OH)CHNC6H10NCH]3 [ No CAS ]
  • 30
  • [ 20439-47-8 ]
  • [ 37091-73-9 ]
  • R,R-N,N′-(cyclohexane-1,2-diyl)bis(1,3-dimethylimidazolidin-2-imine) [ No CAS ]
  • 31
  • [ 463-71-8 ]
  • [ 20439-47-8 ]
  • [ 22235-25-2 ]
  • 3-(3-((1R,2R)-2-aminocyclohexyl)thioureido)-5-(trifluoromethyl)benzoate [ No CAS ]
  • 32
  • [ 20439-47-8 ]
  • [ 141-97-9 ]
  • [ 42059-80-3 ]
  • ethyl (4aR,12aR,E)-6-(2-ethoxy-2-oxoethylidene)-8-(2-hydroxy-5-nitrobenzoyl)-11-methyl-1,2,3,4,4a,5,6,7,7a,12a-decahydrobenzo[b]pyrido[1,2-d][1,4]diazepine-10-carboxylate [ No CAS ]
 

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