Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 622-40-2 | MDL No. : | MFCD00006180 |
Formula : | C6H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KKFDCBRMNNSAAW-UHFFFAOYSA-N |
M.W : | 131.17 | Pubchem ID : | 61163 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 37.9 |
TPSA : | 32.7 Ų |
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) : | -7.66 cm/s |
Log Po/w (iLOGP) : | 1.66 |
Log Po/w (XLOGP3) : | -0.79 |
Log Po/w (WLOGP) : | -1.07 |
Log Po/w (MLOGP) : | -0.67 |
Log Po/w (SILICOS-IT) : | 0.51 |
Consensus Log Po/w : | -0.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.02 |
Solubility : | 124.0 mg/ml ; 0.947 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.58 |
Solubility : | 501.0 mg/ml ; 3.82 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.26 |
Solubility : | 71.4 mg/ml ; 0.545 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.46 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 40℃; | To a stirred solution of 2-morpholinoethan-l-ol (step 1, 2.5 g, 13.88 mmol, 1.0 eq) in DCM (25 ml) at 0 °C then added thionyl chloride (5.06 mL, 69.44 mmol, 5.0 eq) followed by DMF (Cat.). The reaction mixture was heated to 40 °C for overnight. After completion of the reaction (monitored by TLC), the solvent was evaporated in vacuo providing a crude residue, which was diluted with DCM and washed with saturated sodium bicarbonate solution. Organic layer was concentrated under reduced preesure gave crude residue which was purified by column chromatography by using 3percent MeOH in DCM as an eluent to afford the desired compound (2.0 g, yield: 74.0percent) as a colour less liquid. 1H NMR (DMSO-d6, 300MHz): δ 3.69 (t, J = 6.9 Hz, 2H), 3.57 (m, J = 4.5 Hz, 4H), 2.64 (t, J = 6.9 Hz, 2H) and 2.43 (t, J = 4.5 Hz, 4H); Mass: [M+H]+149.95 (10percent). |
43.85% | With thionyl chloride In dichloromethane at 0 - 40℃; | To a stirred solution of 2-morpholinoethan-1-ol (step 1, 3.0 g, 22.869 mmol, 1.0 eq) inDCM (45 mL) at 0 oc was added four drops of DMF and thionyl chloride (9.17 mL, 125.7820 mmol, 5.5 eq). The reaction mixture was warmed to room temperature and heated at 40 ocfor overnight. After completion of the reaction (monitored by TLC), the reaction mixture wasevaporated under reduced pressure, diluted with water (100 mL) and extracted with DCM(3x50 mL). The combined organic layers were washed with saturated sodium bicarbonatesolution (200 mL) and water (100 mL). The organic layer was dried over sodium sulfate,25 filtered and evaporated under reduced pressure. The residue was purified by silica gel columnchromatography by using 2-3percent methanol in DCM gradient. The fractions containing theexpected product were combined and concentrated under reduced pressure to obtain the titlecompound (1.5 g, yield: 43.85percent) as a colourless oil. 1H NMR (300 MHz, CDCb): 8 ppm3.72 (t, J = 4.5 Hz, 4H), 3.59 (t, J = 6.9 Hz, 2H), 2.72 (t, J = 6.9 Hz, 2H), 2.51 (t, J = 4.5 Hz,30 4H); ESI-MS: m/z 150.0 (M+Ht |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium carbonate In acetonitrile for 3 h; Reflux | A mixture of 2-bromoethanol (27.9 g, 223 mmol), morpholine (40 g, 459 mmol) and K2C03 (48.4 g, 350 mmol) in CH3CN (30 mL) was refluxed for 3 h. The mixture was then cooled to rt and filtered. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (24.40 g, 83percent), which was used for next step without further purification. |
83% | With potassium carbonate In acetonitrile for 3 h; Reflux | A mixture of 2-bromoethanol (27.9 g, 223 mmol), morpholine (40 g, 459 mmol) and K2CO3 (48.4 g, 350 mmol) in CH3CN (30 mL) was refluxed for 3 h. The mixture was then cooled to rt and filtered. The filtrate was concentrated in vacuo to give the title compound as a yellow solid (24.40 g, 83percent), which was used for next step without further purification. |
83% | With potassium carbonate In acetonitrile for 3 h; Reflux | In a 500 mL round-bottomed flask, 2-bromoethanol (27.9 g, 223 mmol), morpholine (40 g, 459 mmol), K2CO3 (48.4 g, 350 mmol), and CH3CN (30 mL) were added and refluxed for 3 h. The reaction was completed.The reaction was cooled to room temperature, filtered and the solvent evaporated to dryness. The crude product was used in the next reaction without further treatment to give a yellow solid (24.40 g, 83percent). |
65% | for 3 h; Reflux | Morpholine (5ml, 57 mmol) was dissolved in acetonitrile (20ml) and 3-bromopropanol (5.7 mL, 63 mmol) was added slowly and the mixture was refluxed for 3h. Yield 65percent. HPLC purity: 98.7percent. |
65% | With potassium carbonate In tetrahydrofuran at 75℃; for 3 h; | To a stirred solution of morpholine (2 g, 22.9 mmol, Spectrochem) in dry tetrahydrofuran (20 mL) was added potassium carbonate (6.3 g, 45.9 mmol, Ranchem) and 2- bromoethanol (2.4 mL, 34.4 mmol) and heated to 75 00 for 3 h. Reaction completion was monitored by TLC. The reaction mixture was concentrated under reduced pressure and water (20 mL) was added and extracted in ethyl acetate (3 x 50 mL). Combinedextract was washed with water, brine solution and dried over anhydrous Na2SO4.The crude product was isolated as brown liquid and was used for next step without further purification (2 g, 65percent). 1H NMR (400 MHz, DMSO-d6): 6 4.40 (s, 1 H), 3.64-3.54 (m, 6H), 2.48-2.33 (m, 6H). LCMS: (Method A) 132 (M-f-H), Rt. 1.2 mm, 99.6percent (Max) |
60% | Stage #1: With potassium carbonate In acetonitrile at 20℃; for 0.5 h; Stage #2: Reflux |
To a stirred solution of 2-bromoethan-l-ol (11.78 mL, 165.92 mmol, 7.0 eq) in acetonitrile (68 ml) was added potassium carbonate (9.8 g, 71.10 mmol, 3.0 eq). The reaction mixture was stirred for about 30 minutes at room temperature then added morpholine (3.2 g, 23.70 mmol, 1.0 eq). The reaction mixture was refluxed for overnight. TLC indicated starting material was consumed and the desired product was observed. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated to get crude residue which was purified by column chromatography by using 3percent MeOH in DCM as an eluent to afford the desired compound (2.5 g, yield: 60.0percent) as a brown colour liquid. 1H NMR (DMSO-d6, 300 MHz): δ 4.37 (s, 1H), 3.56 (m, 4H), 3.49 (m, 2H) and 2.38-2.33 (m, 6H); Mass: [M+H]+131.98 (80percent). |
39.89% | Stage #1: With caesium carbonate In acetonitrile at 20℃; for 1 h; Stage #2: Reflux |
To a stirred solution of 2-bromoethan-1-ol ( 43.0 g, 344.35 mmol, 6.0 eq) inacetonitrile (75 mL) was added cesium carbonate (56.0 g, 172.17 mmol, 3.0 eq). The reactionmixture was stirred at room temperature for 1 hour, then added morpholine (5.0 g, 57.392mmol, 1.0 eq). The reaction mixture was refluxed for overnight. After completion of thereaction (monitored by TLC), the reaction mixture was allowed to cool to room temperature,10 filtered through celite pad and the filtrate was concentrated under reduced pressure. Theresidue was purified by silica gel column chromatography by using 3-10percent methanol in DCMgradient. The fractions containing the expected product were combined and concentratedunder reduced pressure to obtain the title compound (3 .0 g, yield: 39.89percent) as a colourless oil.1H NMR (300 MHz, CDCb): 8 ppm 3.72 (t, J = 4.8 Hz, 4H), 3.63 (t, J = 5.1 Hz, 2H), 2.58-15 2.49 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With dibromotriphenylphosphorane In dichloromethane at 0 - 20℃; | Example 47 80: A solution of the alcohol 79 (1 g, 7.62 mmol) in dichloromethane (76 mL) cooled in an ice bath to 0° C. was treated with dibromotriphenyl phosphorane (3.86 g, 9.15 mmol). After being stirred at room temperature overnight, the solid desired product was filtered off to afford clean bromide 80 (1.4 g, quant); 300 MHz 1H NMR (CD3OD) δ (ppm) 4.1 (m, 2H), 3.85 (m, 2H), 3.8 (t, 2H), 3.7 (t, 2H), 3.58 (m, 2H), 3.25 (m, 2H); MS: 194 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.8% | With triphenylphosphine In dichloromethane | 1) Synthesis of N-(2-bromoethyl) morpholine (84) N-(2-Hydroxyethyl)morpholine [1.312 g (10 mmol.)] and carbon tetrabromide [4.974 g (15 mmol.)] were dissolved in methylene chloride (40 m), to which was added, under ice-cooling, triphenylphosphine [3.147 g (12 mmol.), and then the mixture was then stirred for 15 hours at room temperature. The reaction mixture was concentrated under reduced pressure. n-Hexane was added to the residue, and the mixture was subjected to filtration. The filtrate was concentrated under reduced pressure. The crude product thus obtained was purified by column chromatography (silica gel: 70 g; eluent: n-hexane/ethyl acetate = 1/3) to obtain the desired product (84) [1.122 g (57.8percent)] (colorless oily substance). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With dibromotriphenylphosphorane In dichloromethane at 25℃; for 1 h; | Treat a solution of triphenylphosphine dibromide (124 g, 293 mmol) in DCM (2.44 L) with a solution of 4-morpholineethanol (32 g, 244 mmol) in DCM (60 mL) dropwise over one hour while maintaining the reaction temperature below 25° C. Stir the mixture overnight at room temperature. Conduct an additional reaction as above starting with 4-morpholineethanol (10 g, 76 mmol), scaling the reagents appropriately. Combine the reaction mixtures and collect the solids by vacuum filtration to give the title compound 76.7 g (84percent). 1H NMR (399.8 MHz, DMSO-d6) δ 4.05 (m, 2H), 3.84 (m, 2H), 3.78 (t, J=7 Hz, 1H), 3.67 (t, J=7 Hz, 2H), 3.56 (m, 2H), 3.26 (m, 2H). |
60.8% | With dibromotriphenylphosphorane In dichloromethane at 15℃; for 18 h; Inert atmosphere | Under nitrogen, at 0 ° to a solution of 2-morpholino ethanol (4g, 30.49mmol) in dichloromethane (80mL) was added portionwise dibromo-triphenylphosphine (15.45g, 36.59mmol). The mixture was stirred for 18 hours at 15 degreesTime. After completion of the reaction, the reaction mixture was filtered, the filter cake washed with dichloromethane and dried under reduced pressure to give off white solid (5.1g, 60.8percent). |
[ 108302-54-1 ]
N-Ethyl-2-morpholinoethanamine
Similarity: 0.91
[ 42802-94-8 ]
4-(2-Bromoethyl)morpholine hydrobromide
Similarity: 0.80
[ 108302-54-1 ]
N-Ethyl-2-morpholinoethanamine
Similarity: 0.91