4-[(3-methyl-2-butenyl)oxycarbonyl]-1-(2-hydroxyethyl)piperazine
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With diethylamine; Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) In water; acetonitrile for 0.25h; 5 molpercent catalyst; | 100% |
2-(4-allyl-piperazin-1-yl)-ethanol
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With Thiosalicylic acid; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
In various solvent(s) at 40℃; for 0.5h; | 95% |
In water at 15 - 35℃; for 2h; Temperature; | 81.7% |
Conditions | Yield |
---|---|
With potassium carbonate In water at 83℃; for 5h; Temperature; | 94% |
Conditions | Yield |
---|---|
With manganese; chromium; hydrogen; nickel; aluminium In water at 150℃; under 22502.3 Torr; Temperature; Pressure; Reagent/catalyst; Solvent; Autoclave; | 92.3% |
4-(2-hydroxyethyl)-2-piperazinone
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With ammonia at 40℃; under 1500.15 Torr; for 2.5h; | 88% |
piperazine
2-bromoethanol
A
1-(2-hydroxyethyl)piperazine
B
1,4-bis(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water for 2.5h; pH=8.5; pH-value; Reagent/catalyst; Inert atmosphere; | A 86.2% B n/a |
8-methyl-2-(2-n-propoxyphenyl)quinazolin-4(3H)-one
A
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
A n/a B 84% |
2-[2-(ethyloxy)phenyl]quinazoline-4(3H)-one
A
1-(2-hydroxyethyl)piperazine
B
2-{2-Ethoxy-5-[4-(2-hydroxyethyl)-1-piperazinyl-sulphonyl]phenyl}quinazolin-4(3H)-one
Conditions | Yield |
---|---|
A n/a B 78% |
2-[2-(ethyloxy)phenyl]quinazoline-4(3H)-one
A
1-(2-hydroxyethyl)piperazine
B
2-{2-Ethoxy-5-[4-(2-hydroxyethyl)-1-piperazinylsulphonyl]phenyl}quinazolin-4(3)-one
Conditions | Yield |
---|---|
A n/a B 78% |
ethanolamine
A
1-(2-hydroxyethyl)piperazine
B
1,4-bis(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In water at 140℃; for 96h; Inert atmosphere; Heating; | A 30% B 27% |
oxirane
piperazine
A
1-(2-hydroxyethyl)piperazine
B
1,4-bis(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With methanol | |
With methanol |
A
1-(2-hydroxyethyl)piperazine
B
O-ethyl O'-phenyl thiocarbonate
Conditions | Yield |
---|---|
With potassium chloride In water at 25℃; Rate constant; |
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
at 200℃; |
1-(2-bromo-ethyl)-piperazine; dihydrobromide
A
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
at 50℃; |
(4-(2-hydroxyethyl)piperazin-1-yl)(phenyl)methanone
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With hydrogenchloride Heating; |
A
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With phosphate buffer; potassium chloride In methanol at 37℃; for 8h; pH=7.4; Kinetics; Further Variations:; pH-values; |
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 100 percent / diethylamine / Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) / H2O; various solvent(s) / 0.33 h / 5 molpercent catalyst 2: 100 percent / diethylamine / Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) / H2O; acetonitrile / 0.25 h / 5 molpercent catalyst View Scheme |
ethylenediamine
A
piperazine
B
1-(2-hydroxyethyl)piperazine
C
aminoethylpiperazine
D
2-(2-Aminoethylamino)ethanol
E
1,5-diamino-3-azapentane
F
triethylentetramine
Conditions | Yield |
---|---|
With hydrogen at 150 - 160℃; under 22502.3 Torr; |
ethanolamine
A
piperazine
B
1-(2-hydroxyethyl)piperazine
C
aminoethylpiperazine
D
2-(2-Aminoethylamino)ethanol
E
ethylenediamine
F
1,5-diamino-3-azapentane
G
triethylentetramine
Conditions | Yield |
---|---|
With ammonia; hydrogen at 170℃; under 150015 Torr; |
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In ethanol for 12h; Reflux; |
triethanolamine
A
piperazine
B
1-(2-hydroxyethyl)piperazine
C
aminoethylpiperazine
Conditions | Yield |
---|---|
With ammonia; hydrogen; Ni/Re (6.8wtpercent/1.8wtpercent) on silica/alumina (80/20) at 170℃; under 85781.4 - 99537.9 Torr; for 16h; Product distribution / selectivity; Autoclave; |
triethanolamine
A
piperazine
B
1-(2-hydroxyethyl)piperazine
C
aminoethylpiperazine
D
N,N-bis(2-hydroxyethyl)ethylidenediamine
Conditions | Yield |
---|---|
With ammonia; hydrogen; Ni/Re (6.8wtpercent/1.8wtpercent) on silica/alumina (80/20) at 170℃; under 85781.4 - 99537.9 Torr; for 10h; Product distribution / selectivity; Autoclave; |
1-(2-hydroxyethyl)piperazine
di-tert-butyl dicarbonate
tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate
Conditions | Yield |
---|---|
In tetrahydrofuran for 3h; | 100% |
With triethylamine In tetrahydrofuran | 100% |
In tetrahydrofuran for 2h; | 100% |
1-(2-hydroxyethyl)piperazine
4-chlorobutyric acid 3-diethylaminopropyl ester
4-[4-(2-hydroxyethyl)piperazin-1-yl]butyric acid 3-diethylaminopropyl ester
Conditions | Yield |
---|---|
With potassium carbonate In toluene at 100℃; for 48h; | 100% |
1-(2-hydroxyethyl)piperazine
4-fluoro-2-nitrobenzaldehyde
4-[4-(2-hydroxyethyl)piperazin-1-yl]-2-nitrobenzaldehyde
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 100℃; for 1.5h; | 100% |
1-(2-hydroxyethyl)piperazine
benzyl chloroformate
benzyl 4-(2-hydroxyethyl)-1-piperazinecarboxylate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3.5h; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; | 91% |
With sodium hydroxide In water; acetonitrile at 20℃; pH=9; Inert atmosphere; | 90% |
1-(2-hydroxyethyl)piperazine
2,4-dichloro-2-methylpyrimidine
2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 30℃; | 100% |
Stage #1: 1-(2-hydroxyethyl)piperazine; 2,4-dichloro-2-methylpyrimidine In dichloromethane at 30℃; for 2.5h; Stage #2: With triethylamine In dichloromethane | 89.8% |
Stage #1: 1-(2-hydroxyethyl)piperazine; 2,4-dichloro-2-methylpyrimidine In dichloromethane at 30℃; for 2.5h; Stage #2: With triethylamine In dichloromethane | 89.8% |
1-(2-hydroxyethyl)piperazine
(2′Z-3′E)-6-bromoindirubin-3′-[O-(2-bromoethyl)oxime]
(2'Z-3'E)-6-bromoindirubin-3'-(O-{2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl}oxime)
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 50℃; | 100% |
In N,N-dimethyl-formamide at 90℃; for 0.666667h; Inert atmosphere; Microwave irradiation; |
1-(2-hydroxyethyl)piperazine
methyl 2-cyanoacetate
3-[4-(2-hydroxyethyl)piperazin-1-yl]-3-oxopropanenitrile
Conditions | Yield |
---|---|
neat (no solvent); | 100% |
1-(2-hydroxyethyl)piperazine
5,7-dichloro-2-phenylpyrazolo[1,5-a]pyrimidine
5-Chloro-7-[1-(2-hydroxyethyl)-piperazin-4-yl]-2-phenyl-pyrazolo[1,5-a]-pyrimidine
Conditions | Yield |
---|---|
In 1,4-dioxane at 1 - 30℃; for 1h; | 100% |
1-(2-hydroxyethyl)piperazine
cis-10-(3-Dimethylamino-propyliden)-2-trifluormethyl-thiaxanthen
2-{4-[3-(2-trifluoromethyl-thioxanthen-9-ylidene)-propyl]-piperazin-1-yl}-ethanol
Conditions | Yield |
---|---|
at 140℃; for 36h; Temperature; Large scale; | 100% |
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 24h; | 99% |
1-(2-hydroxyethyl)piperazine
6-chloro-N-methyl-4-propylnicotinamide
6-[4-(2-hydroxyethyl)piperazin-1-yl]-N-methyl-4-propylnicotinamide
Conditions | Yield |
---|---|
In tetrahydrofuran at 20 - 100℃; for 18h; | 99% |
1-(2-hydroxyethyl)piperazine
3,4-bis(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
3-(phenylsulfonyl)-4-(2-(piperazin-1-yl)ethoxy)-1,2,5-oxadiazole-2-oxide
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0℃; for 4h; | 99% |
With sodium hydride In tetrahydrofuran at 0℃; for 4h; | 99% |
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; | 56% |
1-(2-hydroxyethyl)piperazine
4,6-diiodo-2-methylpyrimidine
Conditions | Yield |
---|---|
With triethylamine In isopropyl alcohol at 60℃; for 1h; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1-(2-hydroxyethyl)piperazine; 3,3'-bis(3-bromopropoxy)-2,2'-dimethyl-1,1'-biphenyl With N-ethyl-N,N-diisopropylamine In methanol at 65℃; for 72h; Inert atmosphere; Stage #2: trifluoroacetic acid In water; acetonitrile | 99% |
1-(2-hydroxyethyl)piperazine
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 2h; | 99% |
1-(2-hydroxyethyl)piperazine
2-(chloromethyl)-1-(ethoxyethyl)-1H-benzimidazole
2-{4-[1-(2-Ethoxy-ethyl)-1H-benzoimidazol-2-ylmethyl]-piperazin-1-yl}-ethanol
Conditions | Yield |
---|---|
In 1,4-dioxane at 50℃; for 2h; | 98% |
Conditions | Yield |
---|---|
at 110℃; for 3h; | 98% |
1-(2-hydroxyethyl)piperazine
methyl 6,11-dioxo-6,11- dihydrobenzo[f]pyrido [1,2-a]indole-12-carboxylate
Conditions | Yield |
---|---|
at 80℃; for 3h; | 98% |
1-(2-hydroxyethyl)piperazine
methyl 7,10-dihydroxy-6,11-dioxo-6,11-dihydro-benzo[f]pyrido[1,2-a]indole-12-carboxylate
Conditions | Yield |
---|---|
at 80℃; for 3h; | 98% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 5h; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In water at 100℃; for 12h; | 98% |
With potassium carbonate In water at 80℃; for 24h; | 95% |
With potassium carbonate In dimethyl sulfoxide at 100℃; for 12h; | 70% |
Conditions | Yield |
---|---|
Stage #1: 2-amino-7-hydroxy-4-(4-methoxyphenyl)-1,4-dihydroquinoline-3-carbonitrile With potassium carbonate In acetone at 20℃; for 0.25h; Stage #2: 2,4-dichloro-2-methylpyrimidine In acetone at 80℃; for 0.25h; Stage #3: 1-(2-hydroxyethyl)piperazine In acetone at 80℃; for 12h; | 98% |
1-(2-hydroxyethyl)piperazine
2-(chloromethyl)-6-nitro-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h; | 97.8% |
With potassium carbonate In tetrahydrofuran at 20℃; for 1h; | 87.6% |
1-(2-hydroxyethyl)piperazine
2-Thiophenecarbonyl chloride
Thiophene-2-carboxylic acid 2-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-ethyl ester
Conditions | Yield |
---|---|
In benzene for 1h; Heating; | 97% |
1-(2-hydroxyethyl)piperazine
2,6-bis(3-chloropropionamido)anthracene-9,10-dione
2,6-bis<3-<4-(2-hydroxyethyl)piperazino>propionamido>anthracene-9,10-dione
Conditions | Yield |
---|---|
In ethanol for 14h; Heating; | 97% |
1-(2-hydroxyethyl)piperazine
2-chloro-4-(4-fluorophenyl)quinoline
2-[4-(2-hydroxyethyl)-1-piperazinyl]-4-(4-fluorophenyl)quinoline dihydrochloride
Conditions | Yield |
---|---|
at 130℃; for 2h; | 97% |
In water |
Conditions | Yield |
---|---|
at 80℃; for 4h; | 97% |
1-(2-hydroxyethyl)piperazine
2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide
dasatanib
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In acetonitrile at 30 - 80℃; | 97% |
In propan-1-ol at 115 - 120℃; Temperature; | 93% |
With copper(l) chloride In N,N-dimethyl-formamide at 65℃; for 2h; Temperature; Reagent/catalyst; | 91.6% |
The 1-(2-Hydroxyethyl)piperazine with CAS registry number of 103-76-4 is also known as (b-Hydroxyethyl)piperazine. The IUPAC name is 2-Piperazin-1-ylethanol. It belongs to product categories of Piperaizine. Its EINECS registry number is 203-142-3. In addition, the formula is C6H14N2O and the molecular weight is 130.19. This chemical is a clear colorless to pale yellow oily liquid that miscible with water. It may cause inflammation to the skin or other mucous membranes and should be sealed in ventilated, cool, dry place away from fire, heat, oxidants. What's more, this chemical is used as for organic synthesis.
Physical properties about 1-(2-Hydroxyethyl)piperazine are: (1)ACD/LogP: -0.45; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.43; (4)ACD/LogD (pH 7.4): -2.15; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 15.71; (13)Index of Refraction: 1.475; (14)Molar Refractivity: 36.22 cm3; (15)Molar Volume: 128.6 cm3; (16)Polarizability: 14.35×10-24 cm3; (17)Surface Tension: 34.7 dyne/cm; (18)Density: 1.012 g/cm3; (19)Flash Point: 101.9 °C; (20)Enthalpy of Vaporization: 56.01 kJ/mol; (21)Boiling Point: 245 °C at 760 mmHg; (22)Vapour Pressure: 0.00492 mmHg at 25°C; (23)Exact Mass: 130.110613; (24)MonoIsotopic Mass: 130.110613; (25)Topological Polar Surface Area: 35.5; (26)Heavy Atom Count: 9; (27)Complexity: 71.5; (28)Covalently-Bonded Unit Count: 1.
Preparation of 1-(2-Hydroxyethyl)piperazine: it is prepared by reaction of piperazine hexahydrate with ethylene oxide. Firstly, piperazine hexahydrate is dissolved in water, stirred and cooled to 15-20 °C. Then ethylene oxide is passed into solution and reaction occurs at the temperature of 30-35 °C for 2 hours under stirring. At last, product is obtained by cooling, filtration, vacuum distillation and collecting distillate at 145-155 °C (5.33kPa).
Use of 1-(2-Hydroxyethyl)piperazine: it is used to produce (2,3-dihydro-benzo[1,4]dioxin-2-yl)-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-methanone by reaction with 2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acid ethyl ester. This reaction occurs at the temperature of 110 °C for 3 hours. The yield is about 98%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system, skin and may have risk of serious damage to eyes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1CN(CCN1)CCO
2. InChI: InChI=1S/C6H14N2O/c9-6-5-8-3-1-7-2-4-8/h7,9H,1-6H2
3. InChIKey: WFCSWCVEJLETKA-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | oral | 3720mg/kg (3720mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(5), Pg. 67, 1980. |
mouse | LD50 | intraperitoneal | 100mg/kg (100mg/kg) | National Technical Information Service. Vol. AD277-689, | |
rabbit | LD50 | oral | 3350mg/kg (3350mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(5), Pg. 67, 1980. |
rabbit | LD50 | skin | > 5mL/kg (5mL/kg) | Union Carbide Data Sheet. Vol. 1/6/1970, | |
rat | LD50 | oral | 4920uL/kg (4.92mL/kg) | American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962. |
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