[ CAS No. 5459-93-8 ] {[proInfo.proName]}

Name: 5459-93-8|N-Ethylcyclohexylamine|95%
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SKU: A533853
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Quality Control of [ 5459-93-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 5459-93-8 ]

Product Details of [ 5459-93-8 ]

CAS No. :	5459-93-8	MDL No. :	MFCD00003834
Formula :	C₈H₁₇N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AGVKXDPPPSLISR-UHFFFAOYSA-N
M.W :	127.23	Pubchem ID :	21609
Synonyms :

Calculated chemistry of [ 5459-93-8 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.26
TPSA :	12.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.47
Log Po/w (XLOGP3) :	1.97
Log Po/w (WLOGP) :	1.93
Log Po/w (MLOGP) :	1.83
Log Po/w (SILICOS-IT) :	1.96
Consensus Log Po/w :	2.03

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.74
Solubility :	2.33 mg/ml ; 0.0183 mol/l
Class :	Very soluble
Log S (Ali) :	-1.85
Solubility :	1.81 mg/ml ; 0.0142 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.12
Solubility :	0.967 mg/ml ; 0.0076 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.04

Safety of [ 5459-93-8 ]

Signal Word:	Danger	Class:	8,3
Precautionary Statements:	P501-P261-P270-P240-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P361+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338-P310-P403+P235-P405	UN#:	2734
Hazard Statements:	H311-H302-H332-H314-H225	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 5459-93-8 ]

* 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 [ 5459-93-8 ]

[ 5459-93-8 ] Synthesis Path-Downstream 1~87

1
[ 108-94-1 ]
[ 75-04-7 ]
[ 5459-93-8 ]

Yield	Reaction Conditions	Operation in experiment
97.8%		(1), to join in a 1L autoclave aqueous ethylamine 123g (1.913mol) of the mass concentration of 70percent, followed by addition of 150g of methanol as a reaction solvent, then adding palladium-carbon catalyst 1.5g, subsequently blowing nitrogen after the air inside the high-pressure reaction vessel displaced, and then introducing hydrogen to maintain the pressure 2.5Mpa, then warmed to 50 , the above-described process has always maintained rapid stirring; (2), followed by a metering pump into the autoclave into the cyclohexanone 150g (1.53mol), and then heated to 130 , and reacted at a reaction pressure of 2.5Mpa 1h, the above reaction process continued through hydrogen and always maintain a high speed stirring; (3), after the end of the reaction, the inner temperature was lowered to room temperature the autoclave, the pressure is vented to atmospheric pressure, and materials, filtration palladium on carbon catalyst, to obtain a purity of 99.6percent of N- cyclohexyl-ethyl filtrate after distillation amine finished 190g, a total yield of 97.8percent. palladium on carbon catalyst of the active ingredient by palladium (Pd) and the activated auxiliary component (C) consisting of the active ingredient palladium (Pd) of 5percent of the total weight of catalyst palladium on carbon

Reference： [1]Patent: CN103435494,2016,B .Location in patent: Paragraph 0054-0057
[2]Pharmaceutical Chemistry Journal,2000,vol. 34,p. 371 - 373
[3]Chemische Berichte,1928,vol. 61,p. 1459
[4]ChemBioChem,2017,vol. 18,p. 2022 - 2027

2
[ 64-17-5 ]
[ 108-91-8 ]
[ 5459-93-8 ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 8941 - 8949
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1911,vol. 153,p. 1207
[3]Journal of the American Chemical Society,1932,vol. 54,p. 306,311
Journal of the American Chemical Society,1933,vol. 55,p. 2051,2056, 2057
[4]Chemiker-Zeitung, Chemische Apparatur,1910,vol. 34,p. 1202
[5]Organometallics,2011,vol. 30,p. 3479 - 3482

3
[ 5459-93-8 ]
[ 75-07-0 ]
[ 91-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	With platinum Hydrogenation;

Reference： [1]Skita; Keil [Chemische Berichte, 1930, vol. 63, p. 34,46, 47][Chemische Berichte, 1932, vol. 65, p. 424,428]

4
[ 103-69-5 ]
[ 5459-93-8 ]

Reference： [1]Patent: DE528465,1927,
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1904,vol. 138,p. 1258
Annales de Chimie (Cachan, France),1905,vol. <8>4,p. 386
[3]Chemische Berichte,1919,vol. 52,p. 1526
[4]Patent: US1782729,1926,
[5]ACS Catalysis,2019,vol. 9,p. 8581 - 8591

5
[ 64-17-5 ]
[ 62-53-3 ]
[ 5459-93-8 ]

Reference： [1]Journal of the American Chemical Society,1930,vol. 52,p. 4349,4354
[2]Green Chemistry,2014,vol. 16,p. 3522 - 3527

6
[ 55414-72-7 ]
[ 5459-93-8 ]
[ 55412-59-4 ]

Reference： [1]Patent: CH609327,1979,
Patent: DE2318636,1974,
Chem.Abstr.,1975,vol. 82

7
[ 5459-93-8 ]
[ 64798-46-5 ]
[ 64798-02-3 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane;	SYNTHESIS EXAMPLE 14 1-Cyclohexyl-1-ethyl-3-(p-fluoro-alpha,alpha-dimethylbenzyl)urea A solution of 1.8 g of p-fluoro-alpha,alpha-dimethylbenzyl isocyanate in 20 ml of n-hexane was added to 1.4 g of <strong>[5459-93-8]N-ethylcyclohexylamine</strong>, and the mixture was allowed to stand overnight. The solvent was then removed by distillation and the resulting crystals were washed with cold n-pentane to obtain 2.7 g of the title compound.

Reference： [1]Patent: US4143061,1979,A
[2]Patent: FR2362122,1978,
Chem.Abstr.,vol. 88

8
[ 5459-93-8 ]
[ 79-04-9 ]
[ 2567-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In benzene;	REFERENCE EXAMPLE 2 N-Ethyl-cyclohexylamine (2.6 g) is dissolved in dry benzene (20 ml). To the solution are added dropwise with stirring chloroacetyl chloride (2.6 g) and triethylamine (2.4 g) under ice-cooling. The mixture is stirred under ice-cooling for one hour and further at room temperature for one hour. The reaction mixture is poured onto ice-water and extracted with ether. The ether layer is washed with an aqueous sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After distilling off the solvent, the resulting residue is distilled under reduced pressure to give N-ethyl-N-cyclohexyl-chloroacetamide (3 g), b.p. 118°-120° C./0.2 mmHg.

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 322 - 326
[2]Patent: US4540703,1985,A

9
[ 16156-58-4 ]
[ 5459-93-8 ]
cyclohexylethylprop-2-ynylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In N,N-dimethyl-formamide

Reference： [1]Burgess, Laurence E. [Synthetic Communications, 1997, vol. 27, # 12, p. 2181 - 2191]

10
[ 5459-93-8 ]
[ 5044-52-0 ]
[2-(Cyclohexyl-ethyl-amino)-ethyl]-triphenyl-phosphonium; bromide [ No CAS ]

Reference： [1]Synthetic Communications,1997,vol. 27,p. 2181 - 2191

11
[ 103-84-4 ]
[ 5459-93-8 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 6749 - 6752

12
[ 556-96-7 ]
[ 5459-93-8 ]
Cyclohexyl-(3,5-dimethyl-phenyl)-ethyl-amine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 1568 - 1569

13
[ 3972-65-4 ]
[ 5459-93-8 ]
N-ethyl-N-(p-t-butylphenyl)cyclohexylamine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 8407 - 8410

14
[ 402-43-7 ]
[ 5459-93-8 ]
cyclohexyl-ethyl-(4-trifluoromethyl-phenyl)-amine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 8407 - 8410

15
[ 97-94-9 ]
[ 1485-75-2 ]
[ 5459-93-8 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 803 - 806

16
[ 64-17-5 ]
[ 108-94-1 ]
[ 75-05-8 ]
[ 5459-93-8 ]
[ 91-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 220℃;

Reference： [1]Kozlov; Basalaeva [Russian Journal of General Chemistry, 1999, vol. 69, # 4, p. 632 - 636]

17
[ 64-17-5 ]
[ 75-05-8 ]
[ 108-93-0 ]
[ 5459-93-8 ]
[ 91-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 220℃;

Reference： [1]Kozlov; Basalaeva [Russian Journal of General Chemistry, 1999, vol. 69, # 4, p. 632 - 636]

18
[ 5459-93-8 ]
[ 75-07-0 ]
[ 91-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	Hydrogenation;

Reference： [1]Skita; Keil [Chemische Berichte, 1930, vol. 63, p. 34,46, 47][Chemische Berichte, 1932, vol. 65, p. 424,428]

19
[ 91-65-6 ]
[ 5459-93-8 ]
[ 108-93-0 ]

Yield	Reaction Conditions	Operation in experiment
	at 280℃;

Reference： [1]Bain; Pollard [Journal of the American Chemical Society, 1939, vol. 61, p. 2704]

20
[ 5459-93-8 ]
[ 277751-25-4 ]
[ 277751-36-7 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1705 - 1713

21
[ 5459-93-8 ]
[ 519007-99-9 ]
5-(cyclohexyl-ethyl-amino)-1-(5-methanesulfonyl-pyridin-2-yl)-3-trifluoromethyl-1<i>H</i>-pyrazole-4-carbonitrile [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 7629 - 7632

22
[ 201230-82-2 ]
[ 5459-93-8 ]
cyclohexyl-ethyl-thiocarbamic acid; compound with cyclohexyl-ethyl-amine [ No CAS ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 2869 - 2873

23
[ 764-48-7 ]
[ 5459-93-8 ]
[ 84761-77-3 ]
3-(N-cyclohexyl-N-ethylamino)-1,1-(ethylenedioxy)indan [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 938 - 942

24
[ 108-91-8 ]
[ 75-05-8 ]
[ 5459-93-8 ]
[ 91-65-6 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 471 - 474
[2]Organic and Biomolecular Chemistry,2012,vol. 10,p. 293 - 304

25
[ 5459-93-8 ]
(1R,2R)-Cyclopentane-1,2-dicarboxylic acid 1-(4-carbamimidoyl-benzylamide) 2-(cyclohexyl-ethyl-amide) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1705 - 1713

26
[ 5459-93-8 ]
{2-Amino-5-[3-(cyclohexyl-ethyl-carbamoyl)-propoxy]-benzylamino}-acetic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

27
[ 5459-93-8 ]
[ 94192-74-2 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

28
[ 261635-98-7 ]
[ 5459-93-8 ]
N-cyclohexyl-N-ethyl-2-methyl-6-(trifluoromethyl)nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; for 4h;	EXAMPLE 111 N-cyclohexyl-N-ethyl-2-methyl-6-(trifluoromethyl)nicotinamide A suspension of 2-methyl-6-(trifluoromethyl)nicotinic acid (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0° C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of N-cyclohexyl-N-ethylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5percent to 100percent acetonitrile/water containing 0.01percent TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 315.1 (M+H)+.

Reference： [1]Patent: US2004/67985,2004,A1 .Location in patent: Page/Page column 23

29
[ 5459-93-8 ]
[ 167091-73-8 ]
[ 841200-87-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate; In acetonitrile; for 20h;Heating / reflux;	To a solution of 3-(4-benzyloxy-phenyl)-propyl-1-bromide (504 mg, 1.65 mmol) and <strong>[5459-93-8]N-ethylcyclohexylamine</strong> (497 muL, 3.30 mmol) in CH3CN (15 mL) was added K2CO3 (510 mg, 3.69 mmol). The reaction mixture was heated at reflux for 20 h. The mixture was filtered and then concentrated under reduced pressure to a golden oil, which was purified on SiO2 (10 g; 50percent acetone/CH2Cl2) to give 484 mg (83percent yield) of the desired product as a clear and colorless oil. TLC (SiO2, acetone): Rf=0.13. MS (ESI): mass calculated for C24H33NO, 351.26; m/z found, 352.4 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.50-7.28 (m, 5H), 7.12 (d, J=8.6, 2H), 6.90 (d, J=8.6, 2H), 5.06 (s, 2H), 2.60-2.45 (m, 7H), 1.78 (br s, 6H), 1.20 (br s, 4H), 1.05 (t, J=7.1, 4H).
83%	With potassium carbonate; In acetonitrile; for 20h;Heating / reflux;	EXAMPLE 35; {3- [4- (BENZOOXAZOL-2-YLOXY)-PHENYL]-PROPYL}-CYCLOHEXYL-ETHYL-AMINE; A. F3- (4-BENZVLOXY-PHENVL)-PROPVIL-CVCLOHEXVL-ETHVL-AMINE; To a solution of 3- (4-BENZYLOXY-PHENYL)-PROPYL-1-BROMIDE (504 MG, 1. 65 MMOL) and <strong>[5459-93-8]N-ethylcyclohexylamine</strong> (497 RL, 3.30 MMOL) in CH3CN (15 mL) was added K2CO3 (510 mg, 3.69 MMOL). The reaction mixture was heated at reflux for 20 h. The mixture was filtered and then concentrated under reduced pressure to a golden oil, which was purified on Si02 (10 g; 50percent ACETONE/CH2CI2) to give 484 mg (83percent yield) of the desired product as a clear and colorless oil. TLC (SIO2, acetone): Rf = 0.13. MS (ESI) : mass CALCULATED FOR C24H33NO, 351.26 ; m/z found, 352.4 [M+H] +.'H NMR (400 MHZ, CDC13) : 7.50-7. 28 (m, 5H) ; 7.12 (d, J = 8.6, 2H), 6.90 (d, J = 8.6, 2H), 5.06 (s, 2H), 2.60-2. 45 (m, 7H), 1.78 (br S, 6H), 1.20 (BR S, 4H), 1.05 (T, J = 7. 1,4H). P

Reference： [1]Patent: US2008/194630,2008,A1 .Location in patent: Page/Page column 38
[2]Patent: WO2005/12296,2005,A1 .Location in patent: Page/Page column 104

30
[ 5459-93-8 ]
[ 14140-15-9 ]
[ 841200-77-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 60℃; for 16h;	To a stirring solution of 4-(2-bromo-ethyl)-phenol (EXAMPLE 5; 4.48 g, 22.3 mmol) in CH3CN (100 mL) was added cyclohexyl-ethyl-amine (5.0 mL, 33.4 mmol), followed by N,N-diisopropylethylamine (7.76 mL, 44.6 mmol). The resulting solution was stirred at 60° C. for 16 h, yielding a suspension. The suspension was allowed to cool to room temperature and was filtered. The filtered solid was washed with ethyl acetate (2.x.20 mL) and dried to give a white solid (4.8 g, 87percent yield). MS (ESI): mass calculated for C16H25NO, 247.19; m/z found, 248.2 [M+H]+. 1H NMR: (400 MHz, CDCl3): 7.01 (d, J=8.6, 2H), 6.87 (d, J=8.6, 2H), 3.32-3.17 (m, 2H), 3.15-2.98 (m, 4H), 2.30-2.21 (m, 2H), 1.77-1.59 (m, 2H), 1.57-1.46 (m, 5H), 1.40-1.10 (m, 3H).
87%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 60℃; for 16h;	EXAMPLE 30; {2- [4- (BENZOTHIAZOL-2-YLOXY)-PHENYL]-ETHYL}-CYCLOHEXYL-ETHYL-AMINE; A. 4-F2- (CVCLOHEXVL-ETHVL-AMINO)-ETHVLL-PHENOL; To a stirring solution of 4- (2- bromo-ethyl)-phenol (EXAMPLE 5; 4.48 g, 22.3 MMOL) in CH3CN (100 mL) was added cyclohexyl-ethyl-amine (5.0 mL, 33.4 MMOL), followed by N, N- DIISOPROPYLETHYLAMINE (7.76 mL, 44.6 MMOL). The resulting solution was stirred at 60 °C for 16 h, yielding a suspension. The suspension was allowed to cool i to room temperature and was filtered. The filtered solid was washed with ethyl acetate (2 x 20 mL) and dried to give a white solid (4.8 g, 87percent yield). MS (ESI) : mass calculated for C16H25No, 247.19 ; M/Z found, 248.2 [M+H] +. 1H NMR: (400 MHz, CDCl3) : 7.01 (d, J = 8.6, 2H), 6.87 (d, J = 8.6, 2H), 3.32-3. 17 (m,. 2H), 3.15-2. 98 (m, 4H), 2.30-2. 21 (m, 2H), 1.77-1. 59 (m, 2H), 1.57-1. 46 (m, 5H), 1.40-1. 10 (m, 3H)

Reference： [1]Patent: US2008/194630,2008,A1 .Location in patent: Page/Page column 37
[2]Patent: WO2005/12296,2005,A1 .Location in patent: Page/Page column 99

31
copper(II) chloride dihydrate [ No CAS ]
[ 1025999-78-3 ]
[ 5459-93-8 ]
[ 313509-60-3 ]

Yield	Reaction Conditions	Operation in experiment
	With formaldehyd; In 1,2-dimethoxyethane; diethyl ether, hydrogen chloride;	EXAMPLE 1 [3-(4-Adamantan-2-ylphenyl)prop-2-ynyl]cyclohexylethylamine Hydrochloride 8.6 ml of 36percent formaldehyde are added to 11.2 ml of cyclohexylethylamine in 100 ml of 1,2-dimethoxyethane and stirring is continued at room temperature for 2 hours. This solution is added to a mixture of 16 g of 2-(4-ethynylphenyl)adamantane (compound II.3) and 0.58 g of copper II chloride dihydrate in 400 ml of 1,2-dimethoxyethane. The reaction mixture is refluxed for 2 hours and the solvents are then evaporated off under reduced pressure. The compound obtained is taken up in diethyl ether, hydrogen chloride is bubbled through and the precipitate obtained is filtered off and dried; m.p.=124° C. (HCl.0.5 H2O).

Reference： [1]Patent: US6482986,2002,B1

32
[ 5459-93-8 ]
[ 103-63-9 ]
[ 108-10-1 ]
[ 141028-65-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium carbonate; In diethyl ether; hexane; ethyl acetate;	EXAMPLE 2 Preparation of N-cyclohexyl-N-ethyl 2-phenylethylamine hydrochloride Into a 250 ml. round bottom flask fitted with a water cooled condenser and magnetic spin bar the following reagents were placed: N-ethyl-cyclohexylamine [3.82 g., 0.03 moles], potassium carbonate [6.8 g., 0.05 moles], 4-methyl-2-pentanone [100 ml.]and 2-phenylethyl bromide [5.55 g., 0.03 moles]. The combined reagents were stirred magnetically, while being heated to reflux, overnight. The solvent was removed by vacuum distillation to yield a brown oil. The product was purified by flash chromatography on silica gel using 10percent ethyl acetate in hexane as the eluding solvent system. The product fractions from the chromatographic separation were combined and the solvent removed by vacuum distillation to yield a light yellow oil. The yellow oil was dissolved in anhydrous diethyl ether and hydrogen chloride gas was introduced to form a white hydrochloride salt. The hydrochloride salt was recrystallized from absolute ethanol to form a hygroscopic solid, m.p. 126° C. the nmr and ms analysis was consistent with the assigned structure.
	With hydrogenchloride; potassium carbonate; In diethyl ether; hexane; ethyl acetate;	EXAMPLE 3 Preparation of N-cyclohexyl-N-ethyl 2-phenylethylamine hydrochloride Into a 250 ml. round bottom flask fitted with a water cooled condenser and magnetic spin bar the following reagents were placed: N-ethyl-cyclohexylamine [3.82 g., 0.03 moles], potassium carbonate [6.8 g., 0.05 moles], 4-methyl-2-pentanone [100 ml.] and 2-phenylethyl bromide [5.55 g., 0.03 moles]. The combined reagents were stirred magnetically, while being heated to reflux, overnight. The solvent was removed by vacuum distillation to yield a brown oil. The product was purified by flash chromatography on silica gel using 10percent ethyl acetate in hexane as the eluding solvent system. The product fractions from the chromatographic separation were combined and the solvent removed by vacuum distillation to yield a light yellow oil. The yellow oil was dissolved in anhydrous diethyl ether and hydrogen chloride gas was introduced to form a white hydrochloride salt. The hydrochloride salt was recrystallized from absolute ethanol to form a hygroscopic solid, m.o. 126° C. The nmr and ms analysis was consistent with the assigned structure.

Reference： [1]Patent: US5256698,1993,A
[2]Patent: US5322859,1994,A

33
[ 5459-93-8 ]
[ 105-36-2 ]
ethyl N-cyclohexyl-N-ethylglycinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; at 20 - 60℃; for 20h;	Ethyl bromoacetate (608 milligrams), <strong>[5459-93-8]N-ethylcyclohexylamine</strong> (507 milligrams), K2CO3 (2.57 g), water (10 milliliter) were combined at room tempreture. After stirring at 6O0C for 20 hours, the reaction mixture was cooled to RT. and diluted with water (10.0 milliliter) and extracted with CH2CI2 (4x to a total volume of 100 milliliter). The combined organic layers were dried with K2CO3. The solvent was removed in vacuo to provide the titled product (720 milligrams). APCIMS: m/z 214.4 (M+1).

Reference： [1]Patent: WO2006/48750,2006,A2 .Location in patent: Page/Page column 32

34
[ 58899-17-5 ]
[ 5459-93-8 ]
[ 541-41-3 ]
[ 69600-56-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethyl acetate;	EXAMPLE 77 2.6 Grams of 5-(3-carboxy-2-methylpropoxy)-3,4-dihydrocarbostyril and 1.6 ml of triethylamine are added to 200 ml of ethyl acetate, followed by dropwise addition of 1.0 ml of ethyl chloroformate under external ice cooling and agitation while maintaining the internal temperature at 10° to 20° C. Thereafter, the mixture is agitated at room temperature for 1 hour, added with 1.4 g of <strong>[5459-93-8]N-ethylcyclohexylamine</strong> and further agitated for 1.5 hours. The reaction solution is poured into water to separate the liquid, and the organic layer is washed with dilute aqueous NaOH solution, diluted hydrochloric acid and water in that order and then dried with anhydrous Na2 SO4. After filtering off the inorganic matter, the mother liquor is concentrated and the residue is recrystallized from ligroin-benzene, obtaining 1.5 g of 5-[3-(N-cyclohexyl-N-ethylaminocarbonyl)-2-methylpropoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with melting point of 114°-115.5° C.

Reference： [1]Patent: US4298739,1981,A

35
[ 58899-17-5 ]
[ 5459-93-8 ]
[ 543-27-1 ]
[ 69600-56-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In chloroform; N,N-dimethyl-formamide;	EXAMPLE 73 1.3 Grams of 5-(3-carboxy-2-methylpropoxy)-3,4-dihydrocarbostyril and 0.8 ml of triethylamine are added to 50 ml of DMF, and the mixture is added dropwise with 0.65 ml of isobutyl chloroformate under external ice cooling and agitation at internal temperature of 0° to 10° C. After this dropwise addition, the mixture is agitated at room temperature for 30 minutes, added dropwise with 0.7 g of <strong>[5459-93-8]N-ethylcyclohexylamine</strong> and further agitated at room temperature for 2 hours. The solvent is distilled off and the residue is dissolved in 200 ml of chloroform, washed with diluted hydrochloric acid, aqueous K2 CO3 solution and water in that order and then dried with anhydrous Na2 SO4. After filtering off the inorganic matter, the mother liquor is concentrated and the residue is recrystallized from ligroin-benzene to obtain 0.8 g of 5-[3-(N-cyclohexyl-N-ethylaminocarbonyl)-2-methylpropoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals. m.p. 114°-115.5° C.

Reference： [1]Patent: US4298739,1981,A

36
[ 58899-17-5 ]
[ 5459-93-8 ]
[ 69600-56-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; thionyl chloride; In dichloromethane;	EXAMPLE 285 2.6 Grams of 5-(3-carboxy-2-methylpropoxy)-3,4-dihydrocarbostyril is suspended in 200 ml of methylene chloride, followed by addition of 2 ml of pyridine. Then 1.4 g of thionyl chloride is added dropwise to this mixed solution while maintaining the internal temperature at 0° to 20° C. After the end of this addition, the mixture is further agitated at the same temperature for 1 hour and then added dropwise with 2 ml of <strong>[5459-93-8]N-ethylcyclohexylamine</strong>, followed by additional 4-hour agitation at room temperature. The reaction solution is washed well with an aqueous K2 CO3 solution and then with water and diluted hydrochloric acid and then dried with anhydrous Na2 SO4. Thereafter, the solvent is distilled off and the resultant residue is isolated and refined by silica gel column chromatography (silica gel: Wakogel C-200; eluent: chloroform-methanol (20:1 (V/V)) and then recrystallized from ligroinbenzene to obtain 0.6 g of 5-[3-(N-cyclohexyl-N-ethylaminocarbonyl)-2-methylpropoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals, m.p., 114°-115.5° C.

Reference： [1]Patent: US4298739,1981,A

37
3-(2-fluorophenyl)-1-methylimidazolidine-2,4-dione [ No CAS ]
[ 5459-93-8 ]
5-(N-Ethyl-N-cyclohexylaminomethylene)-3-(2-fluorophenyl)-1-methylimidazolidine-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In toluene;	EXAMPLE 1 Preparation of 5-(N-Ethyl-N-cyclohexylaminomethylene)-3-(2-fluorophenyl)-1-methylimidazolidine-2,4-dione (Compound 71 herein) In a flask were placed 2.5 grams (g) (0.012 mole) 3-(2-fluorophenyl)-1-methylimidazolidine-2,4-dione, 1.53 g (0.012 mole) N-ethyl-N cyclohexylamine, 12 milliliters (ml) triethylorthoformate, 6 ml toluene and 0.075 g p-toluenesulfonic acid. The contents of the flask were heated while stirring and ethanol was removed via azeotropic distillation. The reaction was continued, adding solvents (triethylorthoformate/toluene, 2:1) as necessary until thin layer chromatography indicated complete consumption of the starting dione. The resulting mixture was concentrated under reduced pressure and purified by column chromatography (silica gel, hexane/ethyl acetate gradient elution) to yield 2.05 g of a solid, melting point 40°-55° C. which was confirmed by infrared, nuclear magnetic resonance and mass spectroscopy to be a mixture of E and Z isomers.

Reference： [1]Patent: US4859228,1989,A

38
3-methyl-6-(3-carboxypropoxy)-2-oxo-1,2-dihydroquinoxaline [ No CAS ]
[ 5459-93-8 ]
3-methyl-6-[3-(N-cyclohexyl-N-ethylaminocarbonyl)-propoxy]-2-oxo-1,2-dihydroquinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.3%	With triethylamine; In tetrahydrofuran; chloroform;	EXAMPLE 65 3-methyl-6-[3-(N-cyclohexyl-N-ethylaminocarbonyl) propoxy]-2-oxo-1,2-dihydroquinoxaline (compound 1029): 3-methyl-6-(3-carboxypropoxy)-2-oxo-1,2-dihydroquinoxaline 2.0 mM obtained in Example 11 was added to tetrahydrofuran 20 ml. An equimolar amount of triethylamine was added thereto, and there was further added dropwise an equimolar amount of pivaloyl chloride at -10° C. and the mixture was stirred at below -10° C. for 1 hour. N-cyclohexylethylamine 0.3 ml was added at once to the obtained reaction mixture, and the mixture was stirred for 3 hours while gradually adjusting the temperature to room temperature. Chloroform was added to the reaction mixture, and the mixture was washed with dilute aqueous potassium carbonate. The aqueous layer was further extracted with chloroform. The combined chloroform layers were dried by adding anhydrous sodium sulfate and concentrated in vacuo. The residue was charged on a column of silica gel (C-200, 70 g) and eluted with chloroform-methanol (50:1) to obtain the compound 1029. Yield: 0.47 g (yield: 63.3percent)

Reference： [1]Patent: US4870175,1989,A

39
4-(1-Phenyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid [ No CAS ]
[ 5459-93-8 ]
[ 543-27-1 ]
N-ethyl-N-cyclohexyl-4-(1-phenyl-1,2,3,4-tetrazol-5-yl)thio-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;	EXAMPLE 58 4-(1-Phenyl-1,2,3,4-tetrazol-5-yl)thio-butyric acid (45 mmole) is dissolved in tetrahydrofuran (50 ml) and thereto is added DBU (50 mmole). To the mixture is added dropwise with stirring isobutyl chloroformate (50 mmole) under ice-cooling. The mixture is stirred at room temperature for 30 minutes. To the mixture is added dropwise <strong>[5459-93-8]N-ethylcyclohexylamine</strong> (54 mmole) and the mixture is further stirred at room temperature for 2 hours. After distilling off the solvent under reduced pressure, the residue is extracted with chloroform. The chloroform layer is washed with 5percent aqueous hydrochloric acid, an aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate. Chloroform is distilled off and the resulting residue is subjected to column chromatogrophy (Wakogel C-200, eluding solvent, chloroform) to isolate N-ethyl-N-cyclohexyl-4-(1-phenyl-1,2,3,4-tetrazol-5-yl)thio-butyramide (yield: 43percent), colorless liquid, nD18 =1.5590. Elementary analysis for C19 H27 N5 OS: