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Quality Control of [ 65838-10-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 65838-10-0 ]

Product Details of [ 65838-10-0 ]

CAS No. :	65838-10-0	MDL No. :
Formula :	C₂₀H₂₇ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	330.89	Pubchem ID :	-
Synonyms :

Safety of [ 65838-10-0 ]

Signal Word:		Class:
Precautionary Statements:		UN#:
Hazard Statements:		Packing Group:

Application In Synthesis of [ 65838-10-0 ]

* 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 [ 65838-10-0 ]

[ 65838-10-0 ] Synthesis Path-Downstream 1~88

1
[ 65838-10-0 ]
[ 138421-25-7 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1993,vol. 75,p. 159 - 162
[2]Tetrahedron Letters,1991,vol. 32,p. 6297 - 6300
[3]Organometallics,2011,vol. 30,p. 115 - 128
[4]Organometallics,2013,vol. 32,p. 2632 - 2642
[5]Heteroatom Chemistry,2014,vol. 25,p. 690 - 697

2
[ 3187-82-4 ]
[ 65838-10-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium tetrahydroborate; In methanol; for 1h;Reflux;	General procedure: sodium borohydride (2.1 eq) was added portion wise over 40 min to a solution of a Schiff base (1.0eq) in MeOH (4 mL/mmol of a Schiff base) at room temperature and the reaction mixture was stirred for 1 h under reflux. After cooling to room temperature, water (5 mL/mmol of a Schiff base)was added and the mixture was extracted with CH2Cl2 (34 mL/mmol of a Schiff base) and evaporated. If any aldehyde remained in the starting reaction mixture, the residue was dissolved in aqueous solution of hydrochloric acid (35%, 1 mL/mmol of a Schiff base) and washed with CH2Cl2(34mL/mmol of a Schiff base). Then excess of K2CO3 (4.5 eq) was added to a water phase. The aqueous phase was extracted with CH2Cl2 (3*3mL/mmol of a Schiff base), dried, and evaporated to give the product in the form of oil. If the product was not sufficiently pure, additional purification by column chromatography was conducted and the product was obtained in the form of oil.
	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 20h;	General procedure: To a solution of the imine (5 mmol) in dry MeOH (30 mL) was slowly added sodium borohydride (12 mmol) at 0 C. After the mixture was stirred for 20 h at room temperature, the reaction mixture was quenched by adding 1 M hydrochloric acid (10 mL) at 0 C. The mixture was extracted with dichloromethane, and the organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product was purified by flash column chromatography (ethyl acetate/dichloromethane = 3:1 then triethylamine) to afford the corresponding secondary amine.

Reference： [1]Tetrahedron Asymmetry,2017,vol. 28,p. 1342 - 1349
[2]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1108 - 1113
[3]Synlett,2017,vol. 28,p. 615 - 619
[4]Tetrahedron,1996,vol. 52,p. 13837 - 13866
[5]Inorganic Chemistry,2015,vol. 54,p. 2017 - 2031
[6]European Journal of Organic Chemistry,2011,p. 681 - 695
[7]Synthetic Communications,2011,vol. 41,p. 3627 - 3634
[8]CrystEngComm,2012,vol. 14,p. 103 - 111
[9]Tetrahedron Asymmetry,2012,vol. 23,p. 345 - 349
[10]Catalysis Letters,2012,vol. 142,p. 794 - 802
[11]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3727 - 3731
[12]Helvetica Chimica Acta,2018,vol. 101

3
[ 28240-69-9 ]
[ 65838-10-0 ]
bis-1,2-[2-((1R,2R)-2,3,3a,4,5,6,7,7a-octahydro-1,3-dibenzyl-1H-1,3,2-benzodiazaphosphole)]ethane [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 927 - 935

4
[ 65838-10-0 ]
[ 644-97-3 ]
(R,R)-C₆H₁₀(NCH₂C₆H₅ [ No CAS ]
(3aR,7aR)-1,3-Dibenzyl-2-phenyl-octahydro-benzo[1,3,2]diazaphosphole 2-oxide [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 927 - 935

5
[ 65838-10-0 ]
[ 1079-66-9 ]
N,N'-dibenzyl-N-(diphenylphosphinyl)-(1R,2R)-cyclohexanediamine [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1998,vol. 9,p. 937 - 948

6
[ 65838-10-0 ]
[ 138442-64-5 ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 10513 - 10524
[2]Tetrahedron Letters,1991,vol. 32,p. 6297 - 6300
[3]Heteroatom Chemistry,2014,vol. 25,p. 690 - 697

7
[ 65838-10-0 ]
[ 677-43-0 ]
(3aR,7aR)-1,3-bis(phenylmethyl)octahydro-2-(dimethylamino)-2H-1,3,2-benzodiazaphosphole 2-oxide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 1958 - 1967
[2]Journal of Organic Chemistry,2006,vol. 71,p. 1513 - 1522

8
[ 100-52-7 ]
(R,R)-1,2-diaminocyclohexane*(+)-tartric acid [ No CAS ]
[ 65838-10-0 ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 10513 - 10524

9
[ 65838-10-0 ]
(3aR,7aR)-2,3,3a,4,5,6,7,7a-Octahydro-1,3-dibenzyl-1H-1,2,3-benzodiazaphosphole-2-sulfide [ No CAS ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 10513 - 10524
[2]Phosphorus, Sulfur and Silicon and the Related Elements,1993,vol. 75,p. 159 - 162

10
[ 65838-10-0 ]
[ 349656-00-4 ]
[ 349655-89-6 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 701 - 705

11
[ 100-44-7 ]
(1R,2R)-1,2-diaminocyclohexane tartrate [ No CAS ]
[ 65838-10-0 ]

Reference： [1]Tetrahedron Asymmetry,2001,vol. 12,p. 1171 - 1178

12
[ 20439-47-8 ]
[ 100-52-7 ]
[ 65838-10-0 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 155 - 158
[2]Chinese Chemical Letters,2011,vol. 22,p. 155 - 158
[3]Patent: WO2008/93272,2008,A2 .Location in patent: Page/Page column 24-25
[4]Inorganic Chemistry,2017,vol. 56,p. 6584 - 6590
[5]Journal of the American Chemical Society,2019,vol. 141,p. 8436 - 8440
[6]Chemical Communications,2007,p. 583 - 585
[7]Patent: US2010/216806,2010,A1 .Location in patent: Page/Page column 107
[8]European Journal of Organic Chemistry,2011,p. 681 - 695
[9]Journal of Medicinal Chemistry,2012,vol. 55,p. 8903 - 8925,23
[10]Heteroatom Chemistry,2014,vol. 25,p. 690 - 697
[11]Tetrahedron Asymmetry,2016,vol. 27,p. 597 - 602

13
[ 107-37-9 ]
[ 65838-10-0 ]
[ 447440-44-0 ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 7920 - 7921

14
[ 57707-55-8 ]
[ 65838-10-0 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 8059 - 8062

15
[ 50777-76-9 ]
[ 65838-10-0 ]
(3aR,7aR)-1,3-Dibenzyl-2-(2-diphenylphosphanyl-phenyl)-octahydro-benzoimidazole [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 8059 - 8062
[2]Tetrahedron Letters,2003,vol. 44,p. 1971 - 1974

16
[ 98-88-4 ]
[ 65838-10-0 ]
(1R,2R)-di(benzylamino)-N-benzoyl-cyclohexane [ No CAS ]

Reference： [1]Enantiomer,2002,vol. 7,p. 85 - 92

17
[ 98-88-4 ]
[ 65838-10-0 ]
[ 496924-12-0 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1921 - 1925
[2]Enantiomer,2002,vol. 7,p. 85 - 92

18
[ 199180-98-8 ]
[ 65838-10-0 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1921 - 1925
[2]Tetrahedron Letters,2003,vol. 44,p. 1971 - 1974
[3]Journal of Organometallic Chemistry,2008,vol. 693,p. 2377 - 2382
[4]Advanced Synthesis and Catalysis,2009,vol. 351,p. 1255 - 1262

19
[ 32974-80-4 ]
[ 65838-10-0 ]
C₂₉H₂₈N₂O₂ [ No CAS ]

Reference： [1]Mendeleev Communications,2003,vol. 13,p. 139 - 140

20
[ 5116-63-2 ]
[ 65838-10-0 ]
C₃₃H₃₀N₂O₂ [ No CAS ]

Reference： [1]Mendeleev Communications,2003,vol. 13,p. 139 - 140

21
[ 20439-47-8 ]
[ 100-39-0 ]
[ 65838-10-0 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1921 - 1925

22
[ 20439-47-8 ]
[ 100-39-0 ]
[ 65838-10-0 ]
[ 849819-90-5 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1921 - 1925

23
[ 100-39-0 ]
[ 65838-10-0 ]
[ 849819-90-5 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1921 - 1925

24
[ 65838-10-0 ]
[ 106-95-6 ]
N,N'-diallyl-N,N'-dibenzyl-cyclohexane-1,2-diamine [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1921 - 1925

25
[ 65838-10-0 ]
[ 74-88-4 ]
(1R,2R)-N,N'-dibenzyl-N,N'-dimethyl-cyclohexane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		CH2Cl2 solution (40.0mL) of N,N?-bis(benzyl)-1,2-diaminocyclohexane (1.29g, 4.38mmol) was treated with iodomethane (1.24g, 8.76mmol) and stirred for 8h at ambient temperature. The reaction mixture was then treated with LiOH·H2O (0.18g, 4.38mmol) in two portions and stirring was continued for next 24h followed by subsequent addition of H2O (20.0mL). The separated organic phase was dried over MgSO4 and concentrated to yield product as yellow sticky oil (1.77g, 83.0% yield). Anal. Calc. for C22H30N2: C, 81.94; H, 9.38; N, 8.69. Found: C, 82.00; H, 9.39; N, 8.71%. 1H NMR (400MHz, CDCl3, ppm): delta=7.36 (4H, d, J=7.60Hz, ArH), 7.28-7.17 (6H, m, ArH), 3.71 (2H, d, J=12.0Hz, CHAHB), 3.63 (2H, d, J=16.0Hz, CHAHB), 2.61-2.59 (2H, m, CyHN), 2.19 (6H, s, N-CH3), 1.92-1.88 (2H, m, CyH), 1.72-1.68 (2H, m, CyH), 1.25-1.19 (2H, m, CyH), 1.12-1.07 (2H, m, CyH).

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1921 - 1925
[2]Polyhedron,2016,vol. 113,p. 81 - 87

26
[ 38274-14-5 ]
[ 65838-10-0 ]
(+)-N,N'-dibenzyl-(7R,8R)-dicyclohexano-5,6,7,8,9,10-hexahydro-6,9-diaza-dibenzo[a,c]cyclodecene [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3473 - 3478

27
[ 612-12-4 ]
[ 65838-10-0 ]
5,12-dibenzyl-1,2,3,4,4a,5,6,11,12,12a-decahydro-dibenzo[b,f][1,4]diazocine [ No CAS ]