[ CAS No. 10045-25-7 ]

Name: 10045-25-7|1,4,7,10-Tetraazacyclododecane tetrahydrochloride|98%
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Quality Control of [ 10045-25-7 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 10045-25-7 ]

CAS No. :	10045-25-7	MDL No. :	MFCD00068484
Formula :	C₈H₂₄Cl₄N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SBWLCGZEBQGYRP-UHFFFAOYSA-N
M.W :	318.12 g/mol	Pubchem ID :	11652630
Synonyms :

Safety of [ 10045-25-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 10045-25-7 ]

* 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.

Upstream synthesis route of [ 10045-25-7 ]
Downstream synthetic route of [ 10045-25-7 ]

[ 10045-25-7 ] Synthesis Path-Upstream 1~2

1
[ 50-00-0 ]
[ 10045-25-7 ]
[ 91987-74-5 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 4, p. 124 - 128
[2] Helvetica Chimica Acta, 1990, vol. 73, # 1, p. 140 - 148

2
[ 5292-43-3 ]
[ 10045-25-7 ]
[ 122555-91-3 ]

Reference： [1] Amino Acids, 2014, vol. 46, # 2, p. 449 - 457

[ 10045-25-7 ] Synthesis Path-Downstream 1~58

1
[ 50-00-0 ]
[ 10045-25-7 ]
[ 91987-74-5 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1991,vol. 110,p. 124 - 128
[2]Helvetica Chimica Acta,1990,vol. 73,p. 140 - 148

2
[ 10045-25-7 ]
[ 294-90-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride	1-10 1,4,7-tetraazacyclododecane Dowex TM 1 × 8 200-400 mesh strong basic type I anion exchange resin (Cl type) was placed in a 300 mL beaker and dissolved in 1 M HCl.After filtering this with Nutche, the obtained filtrate was dissolved in distilled water and poured into a chromatographic tube filled with cotton and sea sand.After adding 1 M HCl until the pH of the droplet became 1, the pH was adjusted to 5 with distilled water. Then add 1 M NaOH until the pH reaches 12 and thenThe pH was adjusted to 7 using distilled water. A solution prepared by dissolving 1,4,7,10-tetraazacyclododecane tetrahydrochloride (1.50 g, 4.72 mmol) in the smallest amount of distilled water was put therein, and droplets having a basic pH were collected.This solution is concentrated on a rotary evaporator andVacuum drying gave a yellow solid. Dissolve this in CHCl3, add Na2SO4 to dehydrate it, filter it with Nutche, wash it with a small amount of CHCl3, collect the filtrate, and concentrate it with a rotary evaporator.Vacuum dried and left in the refrigerator to give a yellow solid(0.772 g, Yield 95%).
91.3%	With potassium hydroxide In water at 0 - 10℃;	5 Step 5: Preparation of cyclen 174g of cyclen · 4 hydrochloride was added to the reaction vessel, 100-200 ml of pure water was added, the temperature was raised to 80-100 ° C, and a solution of KOH (150-200 g) in water (150-200 ml) was added dropwise. After cooling to room temperature, crystals are precipitated. The ice-water bath is further cooled to 0-10 ° C, stirred for 1 hour, filtered, and the mother liquor is used to wash the filter cake. The filter cake is refluxed to remove water with toluene (500-800ml). Toluene (200-300 ml) was recrystallized to obtain 86 g of a white crystalline solid with a purity of 99.98% and a yield of 91.3%.
	With potassium hydroxide

13.77 g	With sodium hydroxide In toluene at 40℃; for 1h; Reflux;	1.4 In a 500 ml reaction flask equipped with a stirrer, a condenser, and a water separator, 38 g of IV (0.20 mol) was placed,25% sodium hydroxide 47. 5 mL (0.6 mol) (controlled internal temperature below 40 degrees), stirred for 1 hour,Add 142. 5mL toluene, heated to reflux, until the anhydrous separation, slightly cold (60 degrees), suction toluene overnight,Residue plus 25% sodium hydroxide 47. 5 mL (temperature, same as above),Add 142. 5mL toluene reflux to the water, static, take out the toluene solution,The combined toluene solution was concentrated at room temperature for about 57 mL and cooled to room temperature. The crystals were precipitated, filtered,The crude product was then recrystallized with 4 times (wet weight) of toluene,To give 13. 77 g of product (vacuum at room temperature). Content> 99% (GC).
12 g	With sodium hydroxide In water; toluene	d Step d, In a 500 mL reaction flask equipped with a stirrer, a condenser tube, and a water separator, 50 L of water and 50 g of water were successively added.Compound 4: 80g of sodium hydroxide with a concentration of 50%, stirred and crystallized, discharged, centrifuged, and the solid product was collected to obtain crude 15 g of cyclophanate, purified by toluene-water extraction, and the organic phase was collected and added to 142.5 mL. Toluene, heated to reflux, until no moisture is removed, cooled to 60°C, and the toluene was aspirated overnight. The residue was further added with 50% sodium hydroxide (temperature, ibid), and 142.5 mL of toluene was added to reflux to separate the water. Stir, suck out the toluene solution, combine the normal pressure of the toluene solution to concentrate about 57mL remaining at room temperature, cool to room temperature, crystallize out, and filter to obtain a crude product which is then recrystallized with 4 times (wet weight) toluene and concentrated to collect a white solid, which is dried under reduced pressure at 50°C. The product was obtained as 12 g of cyclosporine, yielding about 87.6%. . The reaction formula is as follows:

Reference： [1]Current Patent Assignee: DOSHISHA UNIVERSITY - JP2021/42186, 2021, A Location in patent: Paragraph 0058-0059
[2]Current Patent Assignee: CHEMSTONE - CN110698419, 2020, A Location in patent: Paragraph 0061; 0062; 0063
[3]Buoeen, Solfrid; Dale, Johannes; Krane, Jostein [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 9, p. 773 - 778]
[4]Current Patent Assignee: XIAMEN HUAXING CHEMICAL - CN103360333, 2016, B Location in patent: Paragraph 0083-0085; 0087; 0092-0093
[5]Current Patent Assignee: SHANGHAI LINKCHEM TECH - CN107915691, 2018, A Location in patent: Sheet 0041; 0042

3
[ 52667-88-6 ]
[ 10045-25-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With hydrogenchloride; sulfuric acid; Amberlyst A₂₆ at 120℃; for 48h;
48%	Stage #1: cyclen tetratosylate With sulfuric acid at 150℃; for 1h; Stage #2: With hydrogenchloride In ethanol	1-9 1,4,7,10-tetraazacyclododecane tetrahydrochloride Put the rotor in a 1L eggplant flask, and use a reflux tube, a three-way cock,A balloon was attached and vacuum dried.Add 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetratosylate (48.1 g, 61.0 mmol) and conc. H2SO4 (35 mL) to the reaction vessel.The mixture was stirred at 150 ° C for 1 hour. After returning to room temperature, EtOH (260 mL), It was slowly added dropwise in the order of Et2O (420 mL). The resulting gray precipitate was filtered through Nutche and the resulting solid was transferred to a 500 mL Meyer.Dissolved in the smallest amount of H2O. This was filtered through Celite, washed with a small amount of H2O, and the filtrate was collected and concentrated to obtain a black oily substance.To this was added 12 M HCl (50 mL) and EtOH (300 mL) and stirred to give a gray solid (9.41 g, Yield 48%).
	With hydrogenchloride; sulfuric acid 1.) 100 deg C, 48 h; Yield given. Multistep reaction;

7.2 g	With hydrogenchloride; sulfuric acid 1.) 100 deg C, 70 h;
	Stage #1: cyclen tetratosylate With sulfuric acid In water at 80℃; for 24h; Stage #2: With hydrogenchloride In water	c Step c, Into a 2L four-necked bottle, 1000 mL of water, 62 g of sulfuric acid, and 16 g of compound 3 were successively added, and the temperature was raised to 80°C.Should be 24 hours, cooled to room temperature, transferred to another reactor of equal size, added ethanol 65g, crystallized, discharged, centrifuged, collected solid product, put into a 2L reactor, then add water 220mL, activated carbon 2g, stirring After decoloration for 4 hours, the material was discharged, centrifuged, and the filtrate was collected. 25 g of hydrochloric acid was added to form a salt and crystallized. The material was discharged and centrifuged. The solid product was collected and dried in a drying oven at 50° C. to obtain a crude white compound 4. The reaction formula is as follows:

Reference： [1]Hettich, Ronald; Schneider, Hans-Jörg [Journal of the American Chemical Society, 1997, vol. 119, # 24, p. 5638 - 5647]
[2]Current Patent Assignee: DOSHISHA UNIVERSITY - JP2021/42186, 2021, A Location in patent: Paragraph 0056-0057
[3]Matsumoto, Naohide; Hirano, Akira; Hara, Tadanori; Ohyoshi, Akira [Journal of the Chemical Society, Dalton Transactions, 1983, p. 2405 - 2410]
[4]Kabachnik, M. I.; Medved', T. Ya.; Bel'skii, F. I.; Pisareva, S. A. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1984, vol. 33, p. 777 - 782][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1984, # 4, p. 844 - 849]
[5]Current Patent Assignee: SHANGHAI LINKCHEM TECH - CN107915691, 2018, A Location in patent: Sheet 0039; 0040

4
[ 50-00-0 ]
[ 10045-25-7 ]
[ 164858-92-8 ]

Yield	Reaction Conditions	Operation in experiment
29%	With hypophosphorous acid In water at 40℃; for 3h;

Reference： [1]Bazakas, Konstantinos; Lukes, Ivan [Journal of the Chemical Society, Dalton Transactions, 1995, # 7, p. 1133 - 1138]

5
[ 5130-24-5 ]
[ 10045-25-7 ]
1,7-bis(vinyloxycarbonyl)-1,4,7,10-tetraazacyclododecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide

Reference： [1]Kovacs, Zoltan; Sherry, A. Dean [Synthesis, 1997, # 7, p. 759 - 763]

6
[ 10045-25-7 ]
[ 541-41-3 ]
[ 162148-43-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydroxide

Reference： [1]Kovacs, Zoltan; Sherry, A. Dean [Synthesis, 1997, # 7, p. 759 - 763]

7
[ 10045-25-7 ]
[ 501-53-1 ]
[ 162148-45-0 ]
1,4,7,10-tetrakis(benzyloxycarbonyl)-1,4,7,10-tetraazacyclododecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 10% 2: 88%	With hydrogenchloride In 1,4-dioxane for 16h;

Reference： [1]Kovacs, Zoltan; Sherry, A. Dean [Synthesis, 1997, # 7, p. 759 - 763]

8
[ 10045-25-7 ]
[ 79-22-1 ]
[ 162148-42-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydroxide

Reference： [1]Kovacs, Zoltan; Sherry, A. Dean [Synthesis, 1997, # 7, p. 759 - 763]

9
8b,8c-dimethyl-decahydro-2a,4a,6a,8a-tetraaza-cyclopenta[<i>fg</i>]acenaphthylene [ No CAS ]
[ 10045-25-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In ethanol at 60℃; for 48h; Yield given;

Reference： [1]Herve, Gwenaelle; Bernard, Helene; Le Bris, Nathalie; Yaouanc, Jean-Jacques; Handel, Henri; Toupet, Loic [Tetrahedron Letters, 1998, vol. 39, # 38, p. 6861 - 6864]

10
cyclen-glyoxal [ No CAS ]
[ 10045-25-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydroxylamine hydrochloride In methanol for 36h; Heating;
38 g	With hydrogenchloride; hydrazine hydrate In water Reflux;	1.3 In a 500 ml reaction flask equipped with a stirrer, a condenser, a dropping funnel and a thermometer, 85 gAnd hydrazine hydrate 80% 130ml, with hydrochloric acid PH value to 3. 0 ~ 3. 5, heated to reflux 5 ~ 12 hours, cooled to 60 degrees, Then concentrated water and solid precipitation, add 50ml hydrochloric acid, at 25 degrees to continue stirring for more than 3 hours, placed overnight.The filter was filtered and the solid was washed twice with 30 ml of absolute ethanol. To give 45 g of compound D crude,The solid was dissolved in 82. 5g of water and stirred at 60 ° C for 30 minutes. The mixture was purified by adding 100 ml of hydrochloric acid and dried in vacuo to give 38 g of white crystals

Reference： [1]Sandnes, Rolf Wiggo; Gacek, Michel; Undheim, Kjell [Acta Chemica Scandinavica, 1998, vol. 52, # 12, p. 1402 - 1404]
[2]Current Patent Assignee: XIAMEN HUAXING CHEMICAL - CN103360333, 2016, B Location in patent: Paragraph 0065-0082; 0087; 0092-0093

11
cis-13-1,4,7,10-tetraazatetracyclo<5.5.2.0^4,140^10,13>tetradecane [ No CAS ]
[ 10045-25-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydrazine hydrate at 100℃; for 20h; Yield given;

Reference： [1]Herve, Gwenaelle; Bernard, Helene; Bris, Nathalie Le; Baccon, Michel Le; Yaouanc, Jean-Jacques; Handel, Henri [Tetrahedron Letters, 1999, vol. 40, # 13, p. 2517 - 2520]

12
[ 50-00-0 ]
[ 1779-48-2 ]
[ 10045-25-7 ]
[ 138149-64-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	In hydrogenchloride at 100℃; for 2.5h;

Reference： [1]Rohovec, Jan; Kyvala, Mojmir; Vojtisek, Pavel; Hermann, Petr; Lukes, Ivan [European Journal of Inorganic Chemistry, 2000, # 1, p. 195 - 203]

13
[ 10045-25-7 ]
[ 259886-51-6 ]
C₄₈H₄₈N₃₂O₁₆*C₈H₂₀N₄*4ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In water at 100℃; for 2h;

Reference： [1]Kim, Kimoon; Kim, Soo-Young; Jung, In-Sun; Lee, Eunsung; Kim, Jaheon; Sakamoto, Shigeru; Yamaguchi, Kentaro [Angewandte Chemie - International Edition, 2001, vol. 40, # 11, p. 2119 - 2121]

14
[ 3464-50-4 ]
[ 10045-25-7 ]
1,4,7,10-tetrakis(cholesteryloxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With caesium carbonate In chloroform; acetonitrile for 5h; Heating;

Reference： [1]Shinoda, Satoshi; Okazaki, Tsuyoshi; Player, Tomoko N.; Misaki, Hitomi; Hori, Kenzi; Tsukube, Hiroshi [Journal of Organic Chemistry, 2005, vol. 70, # 5, p. 1835 - 1843]

15
[ 3464-50-4 ]
[ 10045-25-7 ]
C₁₂₄H₂₀₄N₄O₈*ClNa [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium carbonate In chloroform; acetonitrile for 7h; Heating;

Reference： [1]Shinoda, Satoshi; Okazaki, Tsuyoshi; Player, Tomoko N.; Misaki, Hitomi; Hori, Kenzi; Tsukube, Hiroshi [Journal of Organic Chemistry, 2005, vol. 70, # 5, p. 1835 - 1843]

16
[ 10045-25-7 ]
(O-(cyclopentyl))chloroacetate [ No CAS ]
1,4,7,10-tetrakis[(cyclopentoxycarbonyl)methyl]-1,4,7,10-tetraazacyclododecane-NaCl complex [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With sodium carbonate In acetonitrile for 4h; Heating;