[ CAS No. 13484-40-7 ] {[proInfo.proName]}

Name: 13484-40-7|1-(2-Methoxyethyl)piperazine|96%
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Quality Control of [ 13484-40-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 13484-40-7 ]

CAS No. :	13484-40-7	MDL No. :	MFCD00191214
Formula :	C₇H₁₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BMEMBBFDTYHTLH-UHFFFAOYSA-N
M.W :	144.21	Pubchem ID :	2734638
Synonyms :

Calculated chemistry of [ 13484-40-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.26
TPSA :	24.5 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.98
Log Po/w (XLOGP3) :	-0.54
Log Po/w (WLOGP) :	-1.22
Log Po/w (MLOGP) :	-0.31
Log Po/w (SILICOS-IT) :	0.63
Consensus Log Po/w :	0.11

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.2
Solubility :	91.8 mg/ml ; 0.637 mol/l
Class :	Very soluble
Log S (Ali) :	0.49
Solubility :	450.0 mg/ml ; 3.12 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-1.29
Solubility :	7.38 mg/ml ; 0.0512 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 13484-40-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13484-40-7 ]

* 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 [ 13484-40-7 ]
Downstream synthetic route of [ 13484-40-7 ]

[ 13484-40-7 ] Synthesis Path-Upstream 1~6

1
[ 110-85-0 ]
[ 627-42-9 ]
[ 13484-40-7 ]
[ 13484-41-8 ]

Yield	Reaction Conditions	Operation in experiment
70.1%	With hydrogenchloride In methanol; water for 8.5 h; Inert atmosphere	Under a nitrogen atmosphere, the reactor 100 ml, piperazine 8.6 g (0.1 mol) g of methanol 10.4 g, was added while stirring 35percent hydrochloric acid 10.4 g (0.1 mol), internal temperature It was referred to as 80 ° C. There, while maintaining the internal temperature below 80 ° C, 2- bromoethanol 8.7g of (0.07 mol) was added dropwise over 0.5 hours, then further continued while stirring for 8 hours in the same temperature conditions, to obtain a reaction solution 36.9g of colorless and transparent. Results The product was analyzed by gas chromatography, is 84.6percent for a yield of N-(2-hydroxyethyl) piperazine, the selectivity, N-(2-hydroxyethyl) piperazine 88.5percent N, N'-bis (2-hydroxyethyl) piperazine, 7.7percent, unknown content was 3.8percent. Along with other examples showing the results of Example 2 in Table 1. Instead of using in Example 2 2-bromoethanol 8.7 g (0.07 mol), 2-methoxyethyl chloride 3.8 g (0.04 mol) reacted in the same manner as in Example 2 except for using It was carried out. Results The product was analyzed by gas chromatography, N-(2-methoxyethyl) piperazine The yield of 70.1percent and the selectivity, N-(2-methoxyethyl) piperazine 83.4percent N, N'- bis (2-methoxy-ethyl) piperazine, and 15.0percent, unknown content was 1.6percent. Along with other examples showing the results of Example 5 shown in Table 1.

Reference： [1] Patent: JP5838628, 2016, B2, . Location in patent: Paragraph 0056; 0059

2
[ 110-85-0 ]
[ 627-42-9 ]
[ 13484-40-7 ]

Reference： [1] J. Appl. Chem. USSR (Engl. Transl.), 1980, vol. 53, # 1, p. 174 - 178[2] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1980, vol. 53, # 1, p. 199 - 203
[3] Patent: JP6070088, 2017, B2, . Location in patent: Paragraph 0056

3
[ 88708-34-3 ]
[ 13484-40-7 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 8, p. 2395 - 2410

4
[ 741287-48-9 ]
[ 13484-40-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2838 - 2843
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 8, p. 2577 - 2581

5
[ 110-85-0 ]
[ 6482-24-2 ]
[ 13484-40-7 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 148 - 155

6
[ 100861-64-1 ]
[ 13484-40-7 ]

Reference： [1] Australian Journal of Chemistry, 1956, vol. 9, p. 397,402

[ 13484-40-7 ] Synthesis Path-Downstream 1~19

1
[ 110-85-0 ]
[ 627-42-9 ]
[ 13484-40-7 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 60 - 80℃; for 8.5h;Inert atmosphere;	Under a nitrogen atmosphere, 25.7 g (0.3 mol) of piperazine and 25.7 g of methanol were charged into a 100 ml reactor, and the internal temperature was 60 C. there,While keeping the internal temperature at 80 C. or lower, 9.5 g of 2-methoxyethyl chloride(0.1 mol) was added dropwise over 0.5 hours,Stirring was further continued for 8 hours under the same temperature condition. After cooling to room temperature,16.0 g of a 25% NaOH aqueous solution was added to the reaction solution to adjust the pH to 12.0 to obtain 74.9 g of a pale yellow transparent reaction liquid.Analysis of the product by gas chromatography revealed that the yield of N- (2-methoxyethyl) piperazine was 78.2%, the piperazine was 24.2% By weight, N- (2-methoxyethyl) piperazine is 15.1Weight% was contained.

Reference： [1]Journal of applied chemistry of the USSR,1980,vol. 53,p. 174 - 178
Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1980,vol. 53,p. 199 - 203
[2]Patent: JP6070088,2017,B2 .Location in patent: Paragraph 0056

2
[ 13484-40-7 ]
[ 61516-73-2 ]
[ 131027-89-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium hydride at 100 - 140℃; for 8h;

Reference： [1]Valenta, Vladimir; Sindelar, Karel; Holubek, Jiri; Ryska, Miroslav [Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 6, p. 1613 - 1629]

3
[ 13484-40-7 ]
[ 2923-96-8 ]
[ 904896-22-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	In dimethyl sulfoxide; at 100℃; for 1h;	Step 1 4-Fluoro-<strong>[2923-96-8]2-nitrobenzaldehyde</strong> (0.20 g, 1.2 mmol), 1-(2-methoxyethyl)piperazine (0.94 mL, 6.5 mmol) and DMSO (3.5 mL) were added and stirred at 100 °C for 1.0 hour. The reaction mixture was added with water and was washed with hexane/ethyl acetate (4/1) to remove impurities. After removing impurities, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate) to obtain 4-[4-(2-methoxyethyl)piperazin-1-yl]-<strong>[2923-96-8]2-nitrobenzaldehyde</strong> (0.23 g, 68percent). 1H-NMR (300 MHz, CDCl3) delta 2.63-2.69 (m, 8H), 3.38 (s, 3H), 3.49 (t, J = 5.1 Hz, 2H), 3.56 (t, J = 5.3 Hz, 2H), 7.04 (dd, J = 8.8, 2.6 Hz, 1H), 7.32 (d, J = 2.6 Hz, 1H), 7.92 (d, J = 9.0 Hz, 1H), 10.2 (s, 1H). APCI-MS (m/z); 294 [M+H]+

Reference： [1]Patent: EP1847532,2007,A1 .Location in patent: Page/Page column 137

4
[ 13484-40-7 ]
[ 784212-05-1 ]
[ 784210-88-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 1-(2-methoxyethyl)piperazine; N-[3-(4-carbonylphenyl)-4-oxoindeno[2,3-d]pyrazol-5-yl](morpholin-4-ylamino)carboxamide With acetic acid In 1-methyl-pyrrolidin-2-one at 20℃; for 16h; Stage #2: With sodium tris(acetoxy)borohydride In 1-methyl-pyrrolidin-2-one at 20℃; for 20h; Stage #3: With sodium hydroxide; water In 1-methyl-pyrrolidin-2-one for 1h;	Synthesis of N-[3-4-[4-(2-methoxyethyl)piperazinyl]methyl}phenyl)-4- oxoindeno [2,3-d] pyrazol-5-yl] (morpholin-4-ylamino) carboxamide dihydrochloride (compound B16): Acetic acid (5.76 g, 96 mmole) was added to a suspension of aldehyde (10 g, 24 mmole) and piperazine (6.91 g, 48 mmole) in NMP (150 mL). The reaction was stirred at room temp for 16h then treated with NaB (OAc) 3H (12.7 g, 60 mmole). The reaction was stirred at room temp for 20h during which time the reaction becomes very viscous. 1N NAOH (200 mL) was then added and the reaction was stirred for LH. The reaction was then poured onto H20 (750 mL) and filtered. The solid was washed with HO (2 x 350 mL), ETOH (100 mL), and ET20 (200 mL). The solid was then dried under vacuum to yield the desired amine as the free base (9.98 g, 76%).
	Stage #1: 1-(2-methoxyethyl)piperazine; N-[3-(4-carbonylphenyl)-4-oxoindeno[2,3-d]pyrazol-5-yl](morpholin-4-ylamino)carboxamide With acetic acid In 1-methyl-pyrrolidin-2-one at 20℃; for 16h; Stage #2: With sodium tris(acetoxy)borohydride In 1-methyl-pyrrolidin-2-one at 20℃; for 20h; Stage #3: With sodium hydroxide; water In 1-methyl-pyrrolidin-2-one for 1h;	Synthesis of N-[3-(4-[4-(2-methoxyethyl)piperazinyI]methyl}phenyl)-4- oxoindeno[2,3-d]pyrazol-5-yl](morpholin-4-ylamino)carboxamide dihydrochloride (compound B16):Acetic acid (5.76 g, 96 mmole) was added to a suspension of aldehyde (10 g, 24 mmole) and piperazine (6.91 g, 48 mmole) in NMP (150 mL). The reaction was stirred at room temp for 16h then treated with NaB(OAc)3H (12.7 g, 60 mmole). The reaction was stirred at room temp for 2Oh during which time the reaction becomes very viscous. IN NaOH (200 mL) was then added and the reaction was stirred for Ih. The reaction was then poured onto H2O (750 mL) and filtered. The solid was washed with H2O (2 x 350 mL), EtOH (100 mL), and Et2O (200 mL). The solid was then dried under vacuum to yield the desired amine as the free base (9.98 g, 76%). The free base was then suspended in EtOH (200 mL) and heated to boiling. The suspension was then treated with 4N HCl in dioxane (15 mL). The suspension clears then after ~15 min, a thick precipitate forms. Additional EtOH (200 mL) was added to facilitate stirring. Once the suspension cooled to room temp, it was filtered and the solid was washed with EtOH (200 mL) and Et2O (200 mL). The solid was then dried under vacuum to yield the desired bis-hydrochloride salt (10.3 g) designated compound B 16.

Reference： [1]Current Patent Assignee: DIEVINI HOPP BIOTECH HOLDING GMBH & CO. KG - WO2004/92139, 2004, A2 Location in patent: Page 85-86
[2]Current Patent Assignee: DIEVINI HOPP BIOTECH HOLDING GMBH & CO. KG - WO2006/2119, 2006, A2 Location in patent: Page/Page column 93; 99

5
[ 13484-40-7 ]
[ 874959-68-9 ]
[ 933038-77-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dichloromethane; water; at 0 - 20℃; for 1h;	A15. 1-(5-Bromo-pyridine-2-sulfonyl)-4-(2-methoxy-ethyl)-piperazine; 809 mg of 1-(2-methoxyethyl)-piperazine are dissolved in 9.0 ml of dichloromethane and 9.0 ml of an aqueous K2CO3 solution (strength 4.0 M). Subsequently, the reaction mixture is cooled in an ice bath and a solution of 1.20 g of <strong>[874959-68-9]5-bromo-pyridine-2-sulfonyl chloride</strong> (compound B8) in 2.0 ml of dichloromethane is added dropwise. Thereafter, the reaction mixture is allowed to warm up to room temperature during which time the two-phase system is vigorously stirred for 1 hour. For workup, the organic layer is separated and the aqueous layer is extracted once with 10 ml of dichloromethane. The combined organic layers are dried, using Na2SO4, filtered with suction and evaporated to dryness to yield 1.70 g of the title compound as yellow oil, which crystallizes at room temperature. M. p. 940C. ESI- MS: 364.3/366.1 (MH+). TLC: Rf = 0.40 (dichloromethane/ethanol 20:1 parts by volume).
	With potassium carbonate; In dichloromethane; water; at 0 - 20℃; for 1h;	B4. 1-(5-Bromo-pyridine-2-sulfonyl)-4-(2-methoxy-ethyl)-piperazine; 809 mg of 1-(2-methoxyethyl)-piperazine are dissolved in 9.0 ml of dichloromethane and 9.0 ml of an aqueous K2CO3 solution (strength 4.0 M). Subsequently, the reaction mixture is cooled in an ice bath and a solution of 1.20 g of <strong>[874959-68-9]5-bromo-pyridine-2-sulfonyl chloride</strong> (compound C4) in 2.0 ml of dichloromethane is added dropwise. Thereafter, the reaction mixture is allowed to warm up to room temperature during which time the two-phase system is vigorously stirred for 1 hour. For workup, the organic layer is separated and the aqueous layer is extracted once with 10 ml of dichloromethane. The combined organic layers are dried, using Na2SO4, filtered with suction and evaporated to dryness to yield 1.70 g of the title compound as yellow oil, which crystallizes at room temperature. M. p. 940C. ESI- MS: 364.3/366.1 (MH+). TLC: Rf = 0.40 (dichloromethane/ethanol 20:1 parts per volume).

Reference： [1]Patent: WO2007/39578,2007,A1 .Location in patent: Page/Page column 39
[2]Patent: WO2007/39581,2007,A1 .Location in patent: Page/Page column 30

6
[ 13484-40-7 ]
[ 6299-85-0 ]
[ 1152096-02-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; In dichloromethane; at 0℃; for 0.5h;	Preparation of 2-Chloro-6-[4-(2-methoxy-ethyI)-piperazin-l-yl]-pyrimidine-4- carboxylic acid methyl ester:; To a solution of <strong>[6299-85-0]2,6-dichloro-pyrimidine-4-carboxylic acid methyl ester</strong> (580 mg, 2.8 mmol) in DCM (6 mL) at 0 C was added triethylamine (0.39 mL, 2.8 mmol), followed by a solution of l-(2-methoxyethyl)piperazine (406 mg, 2.8 mmol) in DCM (6 mL). The resulting solution was stirred at 0 C for 30 min. The reaction mixture was diluted with water and extracted with DCM (3x80 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to afford 870 mg (99%) of the title compound as a pale yellow solid.

Reference： [1]Patent: WO2009/61453,2009,A1 .Location in patent: Page/Page column 113

7
[ 13484-40-7 ]
[ 5767-35-1 ]
[ 1154030-56-4 ]

Yield	Reaction Conditions	Operation in experiment
42%	In water; at 100℃; for 18h;	A mixture of 1.0 g (6.9 mmol) of the compound from Example 7A and 1.1 g (7.6 mmol) 1-(2-methoxyethyl)piperazine in 10 ml water is stirred at 100 C. for 2 h. A further 0.9 g (6.2 mmol) 1-(2-methoxyethyl)piperazine is added and the reaction mixture is stirred further at 100 C. for 16 h. After concentration in vacuo, the residue is stirred in acetonitrile. The solid which has precipitated out is filtered off, washed first with ethanol and then with diethyl ether and dried in vacuo.Yield: 0.8 g (42% of th.)LC-MS (Method 8): Rt=0.22 min; MS (ESIpos): m/z=253 [M+H]+;1H-NMR (400 MHz, DMSO-d6): delta=7.93 (s, 1H), 7.64 (s, 1H), 5.91 (s, 1H), 4.14 (s, 2H), 3.50-3.40 (m, 6H), 3.24 (s, 3H), 2.47-2.39 (m, 4H).

Reference： [1]Patent: US2010/305085,2010,A1 .Location in patent: Page/Page column 23

8
[ 13484-40-7 ]
[ 71406-74-1 ]
[ 1296135-53-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	In butan-1-ol; at 145 - 150℃;	General procedure: To a solution of 7, 8 or 9 (0.74-0.91 mmol) in 3 mL of n-BuOH kept in a PV with stirring, cyclic amines (1.12 mmol) was added. The sealed PV was placed in an oil bath at 145-150 C and stirred for 30-40 min. n-BuOH was evaporated in vacuo and the residue was re-dissolved in 3:1 EtOAc/DCM and washed successively with saturated NaHCO3 and NaCl solution (1 × 15 mL), respectively. The aqueous layer was washed with EtOAc (3 × 5 mL) and the organic layer was dried over anhydrous MgSO4 then filtered. The solution was evaporated in vacuo to afford either solid or semisolid product. Some physical and spectroscopy data are provided below for 7a-r, 8a-f, 9a-e.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2269 - 2281

9
[ 13484-40-7 ]
[ 1635-61-6 ]
[ 1339046-90-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In ISOPROPYLAMIDE at 120 - 130℃; for 24h; Inert atmosphere;	40.A A mixture of 5-chloro-2-nitroaniline (1.4 g, 8.1 mmol), l-(2-methoxy-iethyl)- piperazine (2.0 g, 14.0 mmol) and anhydrous potassium carbonate (1.38 g, 10.0 mmol) in N,N-dimethylacetamide (3 ml) was stirred at 120-130 °C under nitrogen for 1 day. Sample NMR analysis showed complete conversion of the starting material. The resultant mixture was then cooled to room temperature, poured into cold water (15 ml) and stirred vigorously. The resulting yellow brown precipitate was collected by filtration, washed well with water then dried on the filter funnel. The resulting yellow brown solid was slurried in diethyl ether (20 mL) , filtered, washed with additional diethyl ether, dried to afford 5-[4-(2-memoxy-emyl)-piperaan-l-yl]-2-nitro-phenylamine (1.7 g, 75 %) as a yellow brown powder. NMR (400 MHz, DMSO-d6) δ 2.40-2.50, m, 6H; 3.19, s, 3H; 3.25, m, 4H; 3.41, t (J=5.9 Hz), 2H; 6.16, d (J=2.7 Hz), 1H; 6.34, dd (J=2.54, 7.23 Hz), 1H, 7.20 broad s , 2H; 7.76, d (J=9.8 Hz), 1H -

Reference： [1]Current Patent Assignee: PETER MACCALLUM CANCER CENTER - WO2011/123890, 2011, A1 Location in patent: Page/Page column 153

10
[ 13484-40-7 ]
[ 34421-94-8 ]
[ 1402709-67-4 ]

Yield	Reaction Conditions	Operation in experiment
26%	Stage #1: 1-(2-methoxyethyl)piperazine; 4-bromobenzaldehyde diethyl acetal With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 7.5h; Inert atmosphere; Stage #2: With hydrogenchloride In water for 2.5h;

Reference： [1]Bavetsias, Vassilios; Crumpler, Simon; Sun, Chongbo; Avery, Sian; Atrash, Butrus; Faisal, Amir; Moore, Andrew S.; Brown, Nathan; Sheldrake, Peter W.; Bush, Katherine; Henley, Alan; Box, Gary; Valenti, Melanie; De Haven Brandon, Alexis; Raynaud, Florence I.; Workman, Paul; Eccles, Suzanne A.; Linardopoulos, Spiros; Blagg, Julian; Kosmopoulou, Magda; Bayliss, Richard [Journal of Medicinal Chemistry, 2012, vol. 55, # 20, p. 8721 - 8734,14]

11
[ 13484-40-7 ]
[ 34421-94-8 ]
[ 1402709-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 7.5 h / 100 °C / Inert atmosphere 1.2: 2.5 h 2.1: sodium dithionite / ethanol; water / 20 h / 80 °C

12
[ 13484-40-7 ]
[ 151504-81-3 ]
methyl 4-(4-(2-methoxyethyl)piperazin-1-yl)-2-nitrobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In N,N-dimethyl-formamide; at 20℃; for 2h;	General procedure: A mixture ofdifferent fluoro substituted 2-nitrobenzoate (1.5 mmol) and various amines (7.5 mmol) in DMF (3 mL) was stirred atroom temperature for 2 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine. After dried by sodium sulfate and concentration, the residue was purified by chromatography on silica gel to give as yellowish solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2594 - 2599

13
[ 13484-40-7 ]
[ 451-46-7 ]
ethyl 4-(4-(2-methoxyethyl)piperazin-1-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.9%	With potassium carbonate In dimethyl sulfoxide at 120℃; for 27h; Inert atmosphere;	13.1 Step 1: Preparation of ethyl 4- (4- (2-methoxyethyl) piperazin-1-yl) benzoate 337 mg of ethyl 4-fluorobenzoate was dissolved in 2 ml of dimethylsulfoxide, 0.36 ml of 1- (2-methoxyethyl) piperazine and 415 mg of potassium carbonate were added and the temperature was raised to 120 under argon After stirring for 27 hours, the reaction was quenched by adding 10 ml of water and the reaction mixture was extracted with ethyl acetate. The organic phase was combined and washed five times with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated. (Dichloromethane: methanol = 99: 1-98: 2, V / V) to give 473 mg of a yellow solid in 80% yield.
76%	With potassium carbonate In dimethyl sulfoxide at 120℃;

Reference： [1]Current Patent Assignee: Shanghai Institute of Materia Medica (in: CAS); CHINESE ACADEMY OF SCIENCES - CN106146493, 2016, A Location in patent: Paragraph 0321; 0322; 0323; 0324
[2]Zhao, Bin; Li, Yixuan; Xu, Pan; Dai, Yang; Luo, Cheng; Sun, Yiming; Ai, Jing; Geng, Meiyu; Duan, Wenhu [ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 629 - 634]

14
[ 110-85-0 ]
[ 627-42-9 ]
[ 13484-40-7 ]
[ 13484-41-8 ]

Yield	Reaction Conditions	Operation in experiment
70.1%	With hydrogenchloride; In methanol; water; for 8.5h;Inert atmosphere;	Under a nitrogen atmosphere, the reactor 100 ml, piperazine 8.6 g (0.1 mol) g of methanol 10.4 g, was added while stirring 35% hydrochloric acid 10.4 g (0.1 mol), internal temperature It was referred to as 80 C. There, while maintaining the internal temperature below 80 C, 2- bromoethanol 8.7g of (0.07 mol) was added dropwise over 0.5 hours, then further continued while stirring for 8 hours in the same temperature conditions, to obtain a reaction solution 36.9g of colorless and transparent. Results The product was analyzed by gas chromatography, is 84.6% for a yield of N-(2-hydroxyethyl) piperazine, the selectivity, N-(2-hydroxyethyl) piperazine 88.5% N, N'-bis (2-hydroxyethyl) piperazine, 7.7%, unknown content was 3.8%. Along with other examples showing the results of Example 2 in Table 1. Instead of using in Example 2 2-bromoethanol 8.7 g (0.07 mol), 2-methoxyethyl chloride 3.8 g (0.04 mol) reacted in the same manner as in Example 2 except for using It was carried out. Results The product was analyzed by gas chromatography, N-(2-methoxyethyl) piperazine The yield of 70.1% and the selectivity, N-(2-methoxyethyl) piperazine 83.4% N, N'- bis (2-methoxy-ethyl) piperazine, and 15.0%, unknown content was 1.6%. Along with other examples showing the results of Example 5 shown in Table 1.

Reference： [1]Patent: JP5838628,2016,B2 .Location in patent: Paragraph 0056; 0059

15
[ 13484-40-7 ]
[ 3819-88-3 ]
C₁₃H₁₈IN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In dimethyl sulfoxide; at 90℃; for 4.0h;	A soiution of 16 (200 mg, 0.75 mmoi) and 1-(2-methoxyethyi)piperazine (324 mg,2.25 mmoi) in DMSO (2 mL) was heated at 90 C for 4 hours before poured into waterwith stirring. The mixture was stood at room temperature overnight. The precipitate wasfiitered and washed with water. The cake was coiiected and dried to give 72 (278 mg,95%) as a yeiiow soiid. A suspension of this materiai (278 mg, 0.711 mmoi), 1 (175 mg,2.13 mmoi), K2C03 (196 mg, 1.42 mmoi), Cui (41 mg, 0.213 mmoi) and 8-hydroxyquinoiine (21 mg, 0.142 mmoi) in DMSO (2.5 mL) was heated at 120 C overnight under nitrogen. After cooiing, water was added and the mixture was extracted with CH2Ci2/MeOH twice. The combined organic iayers were dried over Na2SO4 and concentrated. The residue was purified by siiica gei coiumn chromatography to give 73 (208 mg, 85%) as a yeiiow soiid. LCMS (m/z: m+1): 346.2.

Reference： [1]Patent: WO2018/165718,2018,A1 .Location in patent: Page/Page column 92

16
[ 13484-40-7 ]
[ 940-05-6 ]
1-[(2-bromo-4-nitro-phenyl)methyl]-4-(2-methoxyethyl)piperazine [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2020,vol. 11,p. 491 - 496

17
[ 13484-40-7 ]
[ 1700330-18-2 ]
[ 2589638-92-4 ]

Yield	Reaction Conditions	Operation in experiment
12%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; johnphos; sodium t-butanolate In toluene at 80℃; Inert atmosphere;	36.1 [00360] Step 1: tert-butyl 6-(4-(2-methoxyethyl)piperazin-1-yl)-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxylate (36-3): In a 20 mL glass vial, a mixture of tert-butyl 6-chloro-1H-pyrrolo[3.4-c]pyridine-2(3H)-carbolylate (36-1, 300 mg, 1.178 mmol), 1-(2-methoxyethyl)piperazine (36-2, 203.8 mg, 1.41 mmol), sodium tert-butoxide (565.5 mg, 5.89 mmol), and (2-biphenyl)di-tert-butylphosphine (JohnPhos, 17.6 mg, 0.0588 mmol) in toluene was purged with nitrogen gas at rt for 3 min. Pd2(dba) (27.2 mg, 0.03 mmol) was then added. The resulting mixture was stirred under N2 at 80 °C overnight. LC-MS showed the reaction was complete. After cooling to rt, the solvent was evaporated under reduced pressure and the crude product was purified by column chromatography (ISCO) (eluting with 50% DCM in hexanes to 100% DCM followed by 2% MeOH in DCM) to give tot-butyl 6-(4-(2-methoxyethyl)pipera/in-1-yl)-1H-pyrrolo\| 3.4-6,\|pyridine-2(3H)-carboxylate (36-3, 50 mg, yield: 12%) as an off-white solid. MS (ESI+): in z: 363.2 (M+H)+.

Reference： [1]Current Patent Assignee: ANGION BIOMEDICA - WO2021/16256, 2021, A2 Location in patent: Paragraph 00360

18
[ 13484-40-7 ]
[ 50-00-0 ]
[ 77-08-7 ]
C₃₇H₅₆N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 1-(2-methoxyethyl)piperazine; formaldehyd In toluene at 70℃; for 0.166667h; Stage #2: 3,3,3',3'-tetramethyl-2,3,2',3'-tetrahydro-[1,1']spirobiindene-5,6,5',6'-tetraol In toluene Reflux;	1 Synthesis of 6: To around bottom flask was added toluene (250 mL), paraformaldehyde (4.45 g, 156 mmol), and 2-methoxyethyl-piperazine (10 mL, 156 mmol). The reaction was stirred for 10 min at 70° C. which point 3,3,3′,3-tetramethyl-1,1′-spirobisindane-5,5′,6,6′-tetraol (10 g, 30.2 mmol) was added and the reaction was stirred at reflux overnight. The reaction was concentrated by rotary evaporator and triturated with hexanes to give 11.5 g of 6 (95%) as a yellow solid. 1H NMR (CDCl3, 500 MHz): δ (ppm) 6.65 (s, 2H), 3.48 (t, 4H, J=5.5 Hz), 3.34 (s, 6H), 3.19 (d, 2H, J=14.8 Hz), 3.10 (d, 2H, J=14.8 Hz), 2.57 (t, 4H, J=5.5 Hz), 2.25 (d, 2H, J=13.4 Hz), 2.12 (d, 2H, J=13.4 Hz), 1.34 (s, 6H), 1.29 (s, 6H); 13C{1H} NMR (CDCl3, 125 MHz): δ (ppm) 146.11, 145.97, 140.35, 136.76, 116.00, 109.33, 69.94 66.51, 60.23 57.86, 56.73, 55.90, 52.86, 51.10 42.53, 33.21, 30.05; HR-MS (m/z) [M+H]+: Calculated: 653.4273, Found: 653.4271; Elemental Analysis for C37H56N4O6 Calculated: C, 68.07, H, 8.65, N, 8.58; Found: C, 67.83, H, 8.79, N, 8.59. The single-crystal x-ray structure of 6 is shown in FIG. 4.

Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA - US2021/309802, 2021, A1 Location in patent: Paragraph 0213; 0218; 0222

19
[ 13484-40-7 ]
[ 1802924-13-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 8h;	General Procedure for the Preparation of 3a-3f and 3h. General procedure: Potassiumcarbonate (2.9 g, 21 mmol), 2a or 2b (10.5 mmol) and various aminederivatives (12.6 mmol) were added to DMF (30 mL) and stirred at65 C overnight. Upon completion of the reaction, water (60 mL)was added to the flask and the aqueous phase was extracted withethyl acetate (80 mL). Then the organic phase was separated anddried over anhydrous sodium sulfate. The residue is purified bycolumn chromatography (petroleum ether/ethyl acetate 12:1, v/v) to obtain the desired intermediates 3a-3f and 3h.

Reference： [1]Fan, Yan; Huang, Zhi; Nie, Yongwei; Wang, Cheng; Wang, Tianqi; Wang, Xin; Xiang, Rong; Yang, Shengyong [European Journal of Medicinal Chemistry, 2022, vol. 237]

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Isomers

Technical Information

• Acetal Formation • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Grignard Reagents Transform Esters into Alcohols • Heat of Combustion • Nomenclature of Ethers • Preparation of Ethers • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Ethers • Ring Opening of Oxacyclopropane • Synthesis of Alcohols from Tertiary Ethers • The Nucleophilic Opening of Oxacyclopropanes

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H200	Unstable explosive
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 13484-40-7 ] {[proInfo.proName]}

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[ 13484-40-7 ] Synthesis Path-Upstream 1~6

[ 13484-40-7 ] Synthesis Path-Downstream 1~19

Technical Information

Related Functional Groups of [ 13484-40-7 ]

Ethers

Related Parent Nucleus of [ 13484-40-7 ]

Piperazines

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[ 13484-40-7 ]

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[ 13484-40-7 ]