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CAS No. : | 39895-56-2 | MDL No. : | MFCD06213766 |
Formula : | C8H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WMOUKOAUAFESMR-UHFFFAOYSA-N |
M.W : | 137.18 | Pubchem ID : | 6496943 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 40.24 |
TPSA : | 46.25 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.99 cm/s |
Log Po/w (iLOGP) : | 1.53 |
Log Po/w (XLOGP3) : | 0.21 |
Log Po/w (WLOGP) : | 0.33 |
Log Po/w (MLOGP) : | 0.94 |
Log Po/w (SILICOS-IT) : | 1.28 |
Consensus Log Po/w : | 0.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.13 |
Solubility : | 10.1 mg/ml ; 0.0733 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.74 |
Solubility : | 24.9 mg/ml ; 0.182 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.24 |
Solubility : | 0.784 mg/ml ; 0.00571 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
98% | With ammonia; hydrogen In methanol for 20 h; | (4-Aminomethyl-phenyl)-methanol hydrochloride salt 4-Hydroxymethyl-benzonitrile (2.0 g, 15 mol) was reduced using Raney nickel (0. 5g) and hydrogen (50 psi) in MeOH: NH3 (100ml) for 20 hours. The reaction mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure to afford (4-aminomethyl-phenyl)-methanol hydrochloride salt (2.01 g, 98percent) as a white solid of sufficient purity for use without further purification: MS (APCI+) : m/z 138.3 (M+H); H-NMR (DMSO-d6) 8 7.20 (s, 4 H), 5.04 (s, 2 H), 4.42 (s, 2 H), 3.83 (s, 1 H), 2.45 (s, 2 H). |
29% | With lithium aluminium tetrahydride In diethyl ether at 0℃; for 3.25 h; Reflux | Example 99 N-((4-(hydroxymethyl)phenyl)methyl)-N-(1-methylpiperidin-4-yl)-2-(4-methoxyphenyl)acetamide hydrochloride (57MBT72D) To a stirred suspension of LiAlH4 (285 mg, 7.52 mmol) in diethylether (10 mL) at 0° C. was added a solution of 4-cyanobenzyl alcohol (0.5 g, 3.76 mmol) in diethylether (5 mL) over 15 min. The grey reaction mixture was heated to reflux for 3 h. After cooling to r.t., the mixture was treated successively with water (1 mL), 2M NaOH (2 mL) and water (2 mL) under vigorous stirring. The resulting white slurry was filtered and washed with CH2Cl2 (20 mL). Extraction with additional CH2Cl2 (20 mL) and n-butanol (20 mL) and evaporation yielded an oil, which upon flash chromatography (0-15percent MeOH in CH2Cl2) gave 152 mg (29percent) of 4-(aminomethyl)benzylalcohol (57MBT52B) as a white solid. Rf=0.51 (30percent MeOH in CH2Cl2+3.5percent NH4OH). |
29% | Stage #1: With lithium aluminium tetrahydride In diethyl ether at 0℃; for 3.25 h; Heating / reflux Stage #2: With sodium hydroxide In diethyl ether; water at 20℃; |
To a stirred suspension of LiAlHU (285 mg, 7.52 mmol) in diethylether (10 mL)at 0° C. was added a solution of 4-cyanobenzyl alcohol (0.5 g, 3.76 mmol) in diethylether (5 mL) over 15 min. The grey reaction mixture was heated to reflux for 3 h. After cooling to r.t, the mixture was treated successively with water (1 mL), 2M NaOH (2 mL) and water (2 mL) under vigorous stirring. The resulting white slurry was filtered and washed with CH2Cl2 (20 mL). Extraction with additional CH2Cl2 (20 mL) and n- butanol (20 mL) and evaporation yielded an oil, which upon flash chromatography (0- 15percent MeOH in CH2Cl2) gave 152 mg (29percent)of 4-(aminomethyl)benzylalcohol (57MBT52B) as a white solid. Rf=0.51 (30percent MeOH in CH2Cl2 +3.5percent NH4 OH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; for 15 h; | To a suspension of lithium aluminium hydride in tetrahydrofuran (400 mL) stirred in air at 0 °C was added a solution of methyl 4-cyanobenzoate (10 g, 62.1 mmol) in tetrahydrofuran (400 mL) dropwise over 15 minutes. The reaction mixture was stirred at 50 °C for 15 hours and then cooled to 0°C and quenched by the slow addition of water (7 mL), 15percent NaOH (7 mL), and water (21 mL). The resulting precipitate was stirred for an additional 30 minutes and filtered. The filtrated was concentrated in vacuo to give (4- (aminomethyl)phenyl)methanol (6.8 g, 80percent yield) as a light yellow oil. LCMS m/z = 138.0 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: With triphenylphosphine In tetrahydrofuran at 60℃; for 1 h; Stage #2: With water In tetrahydrofuranHeating |
1.6 l-(Aminomethyl)-4-(hydroxymethyl)benzene, 6.6Azide 5 (1.96 g, 12.0 mmol) and PPh3 (6.50g, 24.8 mmol, 2.05 eq) were dissolved in THF (25 ml) and heated at 60°C for ] hour. Water (4.5 ml, 248 mmol, 20 eq) was added and the reaction was heated overnight. The solvent was evaporated and the reidue obtained was purified by flash chromatography (eluent DCM to 4: 1 DCM / methanol saturated with NH3) to yield 6 as a white solid (1.44 g, 10.5 mmol, 85percent). Rf = 0.05 (9:1, DCM / MeOH sat. NH3); vmax = cm"1; NMR (300 MHz, CDC13) δ = 7.35 (d, 3J(H,H) = 8.4 Hz, 2H, ArCH a to CH2NH2), 7.30 (d, 3J(H,H) = 8.4 Hz, 2H, ArCH a to C3/4OH), 4.67 (s, 2H, G3/4OH), 3.85 (s, 2H, CH2NH2), 1 68 (bs, 3H, OH NH2); C NMR (75 MHz, CDCI3) δ = 142.6 (ArCCH2NH2), 139.6 (ArCC3/4OH), 127.3 (ArCH), 127.2 (ArCH), 65.0 (CH2OH), 46.2 (CH2N3/4); HRMS (ESI+): m/z calculated for C8Hi2NO [M + H : 138.0913, found 138.0933. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; | To a cooled suspension of lithium aluminu 3 mmol) in tetrahydrofuran (50 mL) at 0 °C was added a solution of 4-formylbenzonitrile (5 g, 38.1 mmol) in tetrahydrofuran (50 mL). The resultant mixture was stirred at room temperature overnight then recooled to 0 °C and treated with a solution of aqueous sodium hydroxide solution (5 N, 32.1 mL). The resultant mixture was then filtrated and the filtrate concentrated in vacuo to provide (4-(aminomethyl)phenyl)methanol (4.5 g, 73 percent) as a white solid. LCMS m/z = 138.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium hydrogencarbonate In tetrahydrofuran; water at 0℃; | 4-Aminomethylbenzyl alcohol (1.0 g, 6.60 mmol) was slurried in a mixture of THF (10 mL) and water (10 ml_). A solution of saturated sodium hydrogen carbonate was added until the pH of the solution was > pH 9. The mixture was cooled to 0 0C and di- tert-butyldicarbonate (2.89 g, 13.23 mmol) added. The reaction was allowed to stir overnight then THF removed under vacuum. The aqueous mixture was extracted with EtOAc (20 mL) and then acidified to pH 3 by addition of 1 N HCI. This was extracted with EtOAc (2 x 10 mL), the organic layers combined, dried (MgSO4) and evaporated to dryness to afford the desired product (1.60 g, 97percent). m/z 252 [M++H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | at 20℃; for 48 h; | Boc2O was added in one portion at r.t. to a solution of (4-aminomethyl-phenyl)-methanol Compound 3a (21.2 mmol, 2.9 g) in CH2C12 (100 mL). The resulting solution wasstirred for 48h, then washed with a 10percent citric acid solution (50 mL) followed by brine. Theorganic layer was separated, then dried over Na2SC>4 and filtered. The solvent was removed invacua to obtain (4-hydroxymethyl-benzyl)-carbamic acid tert-butyl ester Compound 3b as awhite solid (5.2 g, 99percent yield), which was used in the next step without further purification.MnO2 (9.6 g) was added to a solution of Compound 3b (21.2 mmol, 5.2 g) inchloroform (60 mL), forming a black suspension that was stirred at r.t. overnight then filteredthrough a pad of celite. The solvent was evaporated in vacua to obtain (4-forinyl-benzyl)-carbamic acid tert-butyl ester Compound 3c as a white solid (4.3 g, 87percent yield), which was usedin the next step without purification.; NaB(OAc)3H (2.8 mmol, 0.58 g) was added to a mixture of Compound 3c (2.6 mmol,0.6 g) and tetrahydro-pyran-4-ylamine Compound 3d (2.6 mmol, 0.26 g) in CH2C12 (25 mL)and the resulting suspension was stirred at r.t. An aliquot of the reaction mixture showed theformation of product (MS m/e 321; 100percent). An aqueous solution of formaldehyde (37percentsolution, 8.6 mmol, 0.7 mL) was added to the reaction mixture, followed by NaB(OAc)3H (2.8mmol, 0.58 g) added in one portion under ice cooling. The reaction mixture was stirred at r.t.for about 2h, then made basic with a 2N NaOH solution and extracted with CH2C12. Theorganic layer was washed with brine, then separated and dried over Na2SO4. The drying agentwas filtered and the solvent was removed in vacua to yield (4-[methyl-(tetrahydro-pyran-4-yl)-amino]-methyl}-benzyl)-carbamic acid tert-butyl ester Compound 3e as a pale yellow oil.MS m/e 235 (M+H, 100percent). The product was purified by column chromatography (4:1CH2Cl2:MeOH) to yield a colorless oil (0.52 g, 59percent yield).; Compound 3e was dissolved in CH2Cl2, then HC1 in dioxane was added and themixture was stirred at r.t. for 12 hrs. The solvent was removed and the gummy residue wasmade basic with 2N NaOH and extracted with EtOAc. The organic layer was washed withbrine, then separated and dried over Na2SO4. The drying agent was filtered and the solvent wasremoved in vacua to obtain (4-aminomethyl-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineCompound 3f as a pale yellow oil (0.3 g, 83percent yield). MS m/e 235 (M+H, 100percent).; A solution of 3-(3-trifluoromethyl-phenyl)-acryloyl chloride Compound 3g (0.3 mrnol,0.07 g) in THF (2 mL) was added dropwise to a solution of Compound 3f (0.2 mmol, 0.05 g)and Et3N (0.8 mmol, 0.14 mL) in THF (10 mL) at 0°C. The resulting suspension was allowedto warm to r.t. overnight. The reaction mixture was made basic with a 2N NaOH solution andextracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (2X10 mL) andthe organic layers were washed with brine, then dried over Na2SO4 and filtered. The solventwas removed in vacua to yield a yellow solid (with methane) as the product. The crude productwas purified by preparative TLC (9:1 EtOAc-.MeOH, Rf = 0.2) to yield N-(4-[methyl-(tetrahydro-pyran-4-yi)-amino]-methyl}-benzyi)-3-(3-trifluoromethyl-phenyl)-acrylamideCompound 3h (0.06 g, 49percent yield). MS m/e 433 (M+H, 100percent).; Mel (0.08 mL, 1.28 mmol) was added dropwise to a solution of Compound 3h (0.07mmol, 0.03 g) in a mixture of acetone:acetonitrile (2 mL). The resulting solution was stirred atr.t. for 24h to provide a residue. The residue was washed with ether (2x 1 mL) and dried undera high vacuum to provide Compound 64 (0.04 g, 93percent yield) as an iodide salt. MS m/e 584(M+H, 100percent). |
99% | at 20℃; for 48 h; | Boc2O was added in one portion at r.t. to a solution of (4-aminomethyl-phenyl)-methanol Compound 3a (21.2 mmol, 2.9 g) in CH2Cl2 (100 mL). The resulting solution was stirred for 48 h, then washed with a 10percent citric acid solution (50 mL) followed by brine. The organic-layer was separated, then dried over Na2SO4 and filtered. The solvent was removed in vacuo to obtain (4-hydroxymethyl-benzyl)-carbamic acid tert-butyl ester Compound 3b as a white solid (5.2 g, 99percent yield), which was used in the next step without further purification. |
88% | Inert atmosphere | 1.7 l-'Butoxycarbonylaminomethyl-4-hydroxymethyl benzene, 7.7Amine 6 (1.44g, 10.5 mmol) was dissolved in CHCI3 (50 ml) and Boc20 (2.29 g, 10.5 mmol, 1 eq) was added slowly. The reaction was stirred under nitrogen overnight before the solvent was evaporated and the residue obtained was dissolved in ethyl acetate (50 ml). This solution was washed with a citric acid solution (3 * 50 ml), brine (50 ml), dried over Na2S04, and evaporated to yield 7 as a white solid (2.20 g, 9.2 mmol, 88 percent). Rf = 0.57 (DCM / MeOH sat. N3/4, 8:2); Vmax = cm-1; 'H NMR (300 MHz, CDC13) δ - 7.33 (d, 3J(H,H) = 8.2 Hz, 2H, ArCH a to CH2OH), 7.26 (d, J(H,H) = 8.2 Hz, 2H, ArCH a to CH2NHBoc), 4.86 (bs, 1H, NHBoc), 4.68 (s, 2Η, CH^OH), 4.30 (d, 3J(H,H) = 5.7 Hz, 2H, CH?NHBoc), 1.96 (bs, 1H, OH), 1.46 (s, 9Η, C(CH?)3); l 3C NMR (75 MHz, CDC13) δ = 155.9 (CO), 140.0 (ArCCH2OH), 138.3 (ArCCH2NHBoc), 127.6 (ArCH a to CH2NHBoc), 127.2 (ArCH a to CH2OH), 85.2 (C(CH3)3), 65.0 (C3/4OH), 44.4 (CH2NHBoc), 28.4 (C(C3/4)3); HRMS (ESI+): m/z calculated for C,3Hi9N03Na [M + Na]+ : 260.1257, found 260.1253. |
31% | at 20℃; | The mixture of (4-(aminomethyl)phenyl)methanol (1 g, 7.29 mmol) and di-tert-butyl dicarbonate (1.59 g, 7.29 mmol) in dichloromethane (30 mL) was stirred at room temperature overnight then concentrated under reduced pressure and the crude product was added to a silica gel column and was eluted with dichloromethane:ethyl acetate (1:1) to give tert-butyl 4-(hydroxymethyl)benzylcarbamate (0.8 g, 2.28 mmol, 31percent yield) as a white solid.1H NMR (400 MHz, DMSO-d6) δ ppm 7.37 (s, 1H), 7.22 (dd, J = 27.8, 8.0 Hz, 4H), 5.13 (t, J = 5.7 Hz, 1H), 4.46 (d, J = 5.7 Hz, 2H), 4.10 (d, J = 6.1 Hz, 2H), 1.36 (s, 9H). |
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