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CAS No. : | 50742-37-5 | MDL No. : | MFCD01631862 |
Formula : | C13H13NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OWIFNISFRBVGIX-UHFFFAOYSA-N |
M.W : | 199.25 | Pubchem ID : | 1094836 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
With triethylamine; In toluene; at 60℃; for 18h; | Preparation 28 tert-Butyl {4-[([(3-phenoxybenzyl)aminolcarbonyl)amino)methyl]benzyl) carbamate A mixture of the compound from preparation 27 (500mg, 1.51 mmol), <strong>[50742-37-5]3-phenoxybenzylamine</strong> (EP 0313397, pg 16) (345mg, 1.59mmol) and triethylamine (0.64ml,4.53mmol) in toluene (20ml) was stirred at 60C for 18 hours. The cooled mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography on Isolute SCI gel using methanol as eluant to afford the title compound as a white solid, 342mg. 1H NMR (DMSO-d6, 400MHz) delta: 1.38(s, 9H), 4.17(s, 2H), 4.20(s, 4H), 6.82(dd, 1 H), 6.90(s, 1H), 7.00(m, 2H), 7.14(m, 4H), 7.22-7.40(m, 6H). LRMS: ES- 460 [M-H]- |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(b) 3-Phenoxybenzylamine A solution of the product from step (a) (6.5 g) in THF (75 ml) was added under N2 over 15 minutes to a stirred suspension of LAH (2.3 g) in THF (100 ml). After addition was complete, the mixture was refluxed for 5.5 hours, then cooled to -5 C., excess LAH destroyed by the careful addition of 15% w/v aqu. NaOH (100 ml), and the mixture taken up in water (150 ml) and ether (200 ml). The aqueous phase was separated, extracted with ether and the combined ether solutions washed with 2N aqu. NaOH (2*100 ml) and water (2*200 ml), dried over Na2 SO4 and evaporated in vacuo to give the desired product as a colourless oil (5.9 g). The 200 MHz 1 H NMR was consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; at 20℃; for 17h; | To a solution of <strong>[50742-37-5]3-phenoxybenzylamine</strong> described in Preparation Example 4 (33mg, 0.167mmol) and benzothiazole-6-carboxylic acid (30mg, 0.167mmol) in tetrahydrofuran (1 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (89mg, 0.20mmol) and triethylamine (28mul, 0.20mmol), and the solution was stirred at room temperature for 17 hours. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane : ethyl acetate), and the title compound (37mg, 62%) was obtained as a colorless oil. 1H-NMR Spectrum (CDCl3) delta(ppm) : 4.68(2H, d, J=6.0Hz), 6.50(1H, brs), 6.94(1H, dd, J=2.0, 8.0Hz), 7.02-7.04(3H, m), 7.11-7.15(2H, m), 7.31-7.37(3H, m), 7.88(1H, dd, J=1.6, 8.8Hz), 8.18(1H, d, J=8.8Hz), 8.49(1H, d, J=1.6Hz), 9.13(1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 4h; | Preparation Example 75. (3-Phenoxy-benzyl)-carbamic acid phenyl ester To a solution of phenyl chloroformate (0.29mL, 2.3mmol) in tetrahydrofuran (10mL) were added <strong>[50742-37-5]3-phenoxybenzylamine</strong> described in Preparation Example 4 (0.5g, 2.5mmol) and triethylamine (0.35mL, 2.5mmol) dropwise on an ice bath, and then, the solution was stirred at room temperature for 4 hours. The reaction solution was poured into brine, the solution was extracted with ethyl acetate and concentrated, and the title compound (0.7g, 2.2mmol, 88%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 4.24 (2H, d, J=6.0 Hz), 6.87-7.49 (14H, m), 8.29 (1 H, t, J=6.0 Hz). |
88% | With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 4h; | To a solution of phenyl chloroformate (0.29mL, 2.3mmol) in tetrahydrofuran (10mL) were added <strong>[50742-37-5]3-phenoxybenzylamine</strong> described in Preparation Example 4 (0.5g, 2.5mmol) and triethylamine (0.35mL, 2.5mmol) dropwise on an ice bath, and then, the solution was stirred at room temperature for 4 hours. The reaction solution was poured into brine, the solution was extracted with ethyl acetate and concentrated, and the title compound (0.7g, 2.2mmol, 88%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 4.24 (2H, d, J=6.0 Hz), 6.87-7.49 (14H, m), 8.29 (1 H, t, J=6.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.7% | In cyclohexanone; | EXAMPLE 5 The procedure is carried out as described in Example 1(b) but with the use of 50 g (0.25 mol) of <strong>[50742-37-5]3-phenoxybenzylamine</strong> and 25 g (0.255 mol) of cyclohexanone. Distillation leaves 41 g (0.147 mol) of N-cyclohexylidene(<strong>[50742-37-5]3-phenoxybenzylamine</strong>), corresponding to a yield of 58.7% of theory; b.p. 135-136 C./4 Pa. Analysis for C19 H21 NO (molecular weight 279.38): calculated: C 81.69% H 7.58% N 5.01% O 5.73% found: C 80.81% H 7.56% N 5.02% O 6.12%. NMR spectrum tau [ppm]: 2.6-3.2(m), 5.51(s), 7.65(m), 8.33(m) in the ratio of 9:2:4:6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.8% | In toluene; | (b) Production of N-isobutylidene-(<strong>[50742-37-5]3-phenoxybenzylamine</strong>) STR6 38 g (0.528 mol) of isobutyraldehyde is added dropwise within 30 minutes, with stirring, to a solution of 99.5 g (0.5 mol) of <strong>[50742-37-5]3-phenoxybenzylamine</strong> in 100 ml of toluene. After completion of the dropwise addition, stirring is continued for 20 minutes at room temperature, and the water which has formed (about 8.5 g) is separated in a separating funnel. The toluene with the unreacted isobutyraldehyde and residual water is then removed by rotation in a water-jet vacuum, and the residue is distilled in an oil-pump vacuum to yield 124 g (0.49 mol) of N-isobutylidene-(<strong>[50742-37-5]3-phenoxybenzylamine</strong>) as a colourless, mobile liquid, corresponding to a yield of 97.8% of theory; b.p. 85 C./4 Pa; nD20 =1.5666. Analysis for C17 H19 NO (molecular weight 253.35): calculated: C 80.60%; H 7.56%; N 5.53%; O 6.31%. found: C 79.91%; H 7.62%; N 5.41%; O 6.52%. MS spectrum: molecular peak 253, masses of the fragments 184, 183, 168, 153, 77. NMR spectrum tau [ppm]: 2.47(d), 2.6-3.2(m), 5.50(s), 7.51(m), 8.97(d) in the ratio of 1:9:2:1:6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.6% | EXAMPLE 3 The procedure is carried out as described in Example 1(b) except that 50 g (0.25 mol) of <strong>[50742-37-5]3-phenoxybenzylamine</strong> and 30 g (0.348 mol) of diethyl ketone are used. There is obtained after distillation 62.5 g (0.234 mol) of N-3-pentylidene-(<strong>[50742-37-5]3-phenoxybenzylamine</strong>), corresponding to a yield of 93.6% of theory; b.p. 128 C./5 Pa. Analysis for C18 H21 NO (molecular weight 267.37): calculated: C 80.86%; H 7.92%; N 5.24%; O 5.98%. found: C 80.97%; H 7.88%; N 5.36%; O 5.92%. MS spectrum: molecular peak 267, masses of the fragments 238, 183, 85, 83. NMR spectrum tau [ppm]: 2.6-3.3(m), 5.51(s), 7.70(m), 8.90(m) in the ratio of 9:2:4:6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 48h; | Reference Example H-1 Quinazoline-6-carboxylic acid 3-phenoxybenzylamide To a solution of quinazoline-6-carboxylic acid obtained in Preparation Example H-3 (9mg, 0.052mmol) in N,N-dimethylformamide (3mL) were added <strong>[50742-37-5]3-phenoxybenzylamine</strong> described in Preparation Example 4 (11 mg, 0.052mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (28mg, 0.062mmol) and triethylamine (17mul, 0.125mmol), and the solution was stirred for 2 days at room temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate, and concentrated. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate), and the title compound (11 mg, 0.031 mmol, 50%) was obtained. 1H-NMR Spectrum (CD3OD) delta (ppm) : 4.62 (2H, s), 6.88 (1H, dd, J=8.0, 1.2Hz), 6.98 (2H, dd, J=1.2, 8.0Hz), 7.09 (1H, s), 7.07 (1H, dd, J=7.6, 8.0Hz), 7.15 (1H, d, J=7.6Hz), 7.29-7.35 (3H, m), 8.10 (1H, d, J=8.8Hz), 8.40 (1H, dd, J=2.0, 8.8Hz), 8.57 (1 H, d, J=2.0Hz), 9.32 (1 H, s), 9.61 (1 H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Typical procedure: To a stirred solution of the amine (1.0 equiv) and the aldehyde (1.0 equiv) in dichloroethane (0.2 M) was added acetic acid (5.0 equiv). The solution was stirred for 18 h, then sodium triacetoxyborohydride (1.2 equiv) was added and the mixture was stirred for 1 h. The appropriate isocyanate (1.5 equiv) was added and the mixture was stirred for an additional 4 h before being quenched with a saturated aqueous solution of sodium bicarbonate. The layers were separated and the aqueous layer was extracted three times with dichloromethane. The organic layers were combined and dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With pyridine; In toluene; at 20℃; | Example 17 - 3-[(Z)-2-Chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-N-[(3-phenoxyphenyl) methyl]cyclopropanecarboxamide 55 A solution of 3-[(Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-cyclopropanecarbonyl chloride (100mg, 1.1 eq) in toluene (6ml_) was added dropwise to a solution of (3- phenoxyphenyl)methanamine (170mg, 1 eq) and pyridine (68muIota_, 1 eq) in toluene (6ml_). The reaction mixture was stirred overnight at room temperature after which time TLC analysis showed the reaction had gone to completion. The reaction mixture was diluted with ethyl acetate (15ml_) and washed with water (2 x 10ml_) and brine (10ml_) before being dried over MgS04 and the solvent removed in vacuo. The residue was purified by flash chromatography (solvent 9: 1 hexane/ethyl acetate) to afford the product as a clear oil (86mg, 24 %). 1 H NMR deltaEta (CDCIs, 300 MHz): 7.22 (m, 3H), 7.04 (m, 2H), 6.94 (m, 3H), 6.84 (m, 2H), 5.78 (s, 1 H), 4.33 (ddd, J= 20.7, 15.0, 5.7 Hz, 2 H), 1.99 (m, 2 H), 1.21 (s, 3H), 1.19 (s, 3H); ESI-MS 424.2 [MH]+.. |
24% | With pyridine; In toluene; at 20℃; | Example 17 3-[(Z)-2-Chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-N-[(3-phenoxyphenyl)methyl]cyclopropanecarboxamide 55 A solution of 3-[(Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-cyclopropanecarbonyl chloride (100 mg, 1.1 eq) in toluene (6 mL) was added dropwise to a solution of <strong>[50742-37-5](3-phenoxyphenyl)methanamine</strong> (170 mg, 1 eq) and pyridine (68 muL, 1 eq) in toluene (6 mL). The reaction mixture was stirred overnight at room temperature after which time TLC analysis showed the reaction had gone to completion. The reaction mixture was diluted with ethyl acetate (15 mL) and washed with water (2*10 mL) and brine (10 mL) before being dried over MgSO4 and the solvent removed in vacuo. The residue was purified by flash chromatography (solvent 9:1 hexane/ethyl acetate) to afford the product as a clear oil (86 mg, 24%). 1H NMR deltaH (CDCl3, 300 MHz): 7.22 (m, 3H), 7.04 (m, 2H), 6.94 (m, 3H), 6.84 (m, 2H), 5.78 (s, 1H), 4.33 (ddd, J=20.7, 15.0, 5.7 Hz, 2H), 1.99 (m, 2H), 1.21 (s, 3H), 1.19 (s, 3H); ESI-MS 424.2 [MH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.08 g | With tri-n-propylamine; In pentan-1-ol; for 66h;Reflux; | (3-Phenoxyphenyl)methanamine (2.02 g, 10.2 mmol) was taken up in 60 mL of 1-pentanol, and then 15 mL of volatile material was removed by distillation. The mixture was cooled below boiling, and tripropylamine (3.80 mL, 19.9 mmol) and 4-chloroquinoline (1.65 g, 10.2 mmol) were added. Heating at reflux was resumed. After 66 hr, volatile material was removed by evaporation. The mixture was partitioned between DCM (150, 100 mL) and 5% Na2C03 (80 mL). The combined organic phases were dried over Na2S04, filtered, and concentrated to give a solid. Recrystallization from EA/Hex gave 2.08 g of colorless solid. R 0.34 (10% MeOH/DCM); mp 163.0-164.0 C; 1H NMR (CDC13) delta 8.54 (d, 1H, J=5.5 Hz), 8.00 (m, 1H), 7.76 (d, 1H, J=8.1 Hz), 7.64 (m, 1H), 7.43 (m, 1H), 7.34-7.29 (m, 3H), 7.11 (m, 1H), 7.05 (s, 1H), 7.02-6.99 (m, 2H), 6.94 (dd, 1H, J=2.2, 8.0 Hz), 6.42 (d, 1H, J=5.5 Hz), 5.46 (br s, 1H, NH) 4.51 (m, 2H, AB); 13C NMR (CDC13) delta 158.2, 156.9, 151.3, 149.5, 148.7, 139.9, 130.5, 130.3, 130.0, 129.3, 125.0, 123.8, 122.2, 119.5, 119.3, 118.9, 118.0, 117.8, 99.7, 47.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.25 g | With hydrazine hydrate; In isopropyl alcohol; for 7h;Reflux; | Hydrazine monohydrate (3.50 mL, 72.1 mmol) was added to a mixture of N-(3-phenoxybenzyl)phthalimide (6.28 g, 19.1 mmol) and 200 mL of IPA while using mechanical stirring. The mixture was heated at reflux for 7 hr. After standing overnight, a precipitate had formed. The mixture was concentrated by evaporation, and the residue was partitioned between isopropyl acetate and 5% Na2C03 and brine. The organic phases were dried over Na2S04, filtered, and concentrated. SPE, washing with 50% isopropyl acetate/Hex and then eluting with 3% MeOH/DCM + 2% TEA gave fractions that contained ninhydrin (+) product. The combined product fractions were washed with 5% Na2C03, dried over Na2S04, filtered, and concentrated to give 3.25 g of yellow oil. R 0.28 (10% MeOH/DCM); 1H NMR (CDC13) delta 7.36- 7.25 (m, 3H), 7.12-6.95 (m, 5H), 6.87 (ddd, 1H, J=1.0, 2.5, 8.2 Hz), 3.82 (br s, 2H), 2.15 (br s, 2H, NH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.29 g | With triethylamine; In isopropyl alcohol; for 5.5h;Reflux; | (3-Phenoxyphenyl)methanamine (1.55 g, 7.79 mmol) was taken up in 60 mL of IPA, and 15 mL of volatile material was removed by distillation. The mixture was cooled, and TEA (1.50 mL, 10.7 mmol) and 4-chloroquinazoline (1.20 g, 7.32 mmol) in 15 mL of IPA were added. The mixture was heated at reflux for 5.5 hr, and then stirred at room temperature overnight. Then, the volatile components were evaporated, and the residue was partitioned between DCM (3x70 mL) and 5% Na2C03 (40 mL). The combined organic phases were dried over Na2S04, filtered, and concentrated. SPE, eluting with 25% and then 55% EA/Hex, gave product fractions that were combined and concentrated to yield an orange solid. Recrystallization from EA/Hex gave a pink solid, and then from MeOH gave 1.29 g of a light pink solid. R 0.19 (50% EA/Hex); mp 146.5- 148.0 C; 1H NMR (CDC13) delta 8.66 (s, 1H), 7.83 (d, 1H, J=8.5 Hz), 7.77 (d, 1H, J=8.1 Hz), 7.71 (m, 1H), 7.42 (m, 1H), 7.30 (m, 3H), 7.10 (m, 2H), 7.04 (br s, 1H), 6.99 (m, 2H), 6.90 (m, 1H), 6.44 (m, IH, NH), 4.84 (m, 2H, AB); C NMR (CDC13) delta 159.5, 157.9, 157.0, 155.5, 149.6, 140.4, 132.9, 130.3, 130.0, 128.7, 126.3, 123.7, 122.6, 120.9, 119.2, 118.3, 117.9, 115.1, 45.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | General procedure: To a solution of phenethylamine (200 mg, 1.65 mmol) and Et3N (0.64 mL, 4.95 mmol) in anhydrousTHF (2.5 mL) cooled with an ice bath, a solution of CS2 (0.12 mL, 1.98 mmol) was slowly dropped in.The reaction solution was stirred at room temperature for 0.5 h, after which AcCl (0.14 mL, 1.98 mmol)was dropped in at 0 C, and after 5 min the mixture was warmed to room temperature for 15-30 min.When the starting amine was finished, as verified by checking thin layer chromatography (T.L.C.),1MHCl (aq., 2 mL) was added to quench the reaction. The solution was extracted by EtOAc three times.All organic phases were combined and washed with brine, dried over Na2SO4, and finally filtered andconcentrated under reduced pressure. The residue was purified by column chromatography on silicagel (EtOAc/petroleum = 1/1) to provide phenethyl isothiocyanate (PEITC) (253 mg, 94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
123 mg | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 10 - 50℃;Inert atmosphere; | C) 3-oxo-2-(3-phenoxybenzyl)isoindoline-5-carbonitrile Under nitrogen atmosphere, a mixture of <strong>[421551-82-8]methyl 2-(bromomethyl)-5-cyanobenzoate</strong> (100 mg), 1-(3-phenoxyphenyl)methanamine (94 mg), DIEA (0.082 mL) and THF (7 mL) was stirred at 50C for 6 hr, and then overnight at room temperature, and the reaction mixture was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (123 mg). MS (API+), found: 341.2 (M+1) |
[ 31963-35-6 ]
1-(2-Phenoxyphenyl)methanamine hydrochloride
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[ 31963-35-6 ]
1-(2-Phenoxyphenyl)methanamine hydrochloride
Similarity: 0.91
[ 31963-35-6 ]
1-(2-Phenoxyphenyl)methanamine hydrochloride
Similarity: 0.91