Structure of 23972-42-1
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CAS No. : | 23972-42-1 |
Formula : | C10H14ClNO |
M.W : | 199.68 |
SMILES Code : | [H]Cl.C1(C2=CC=CC=C2)CNCCO1 |
MDL No. : | MFCD03869024 |
InChI Key : | LJKUJBAIFSUTNM-UHFFFAOYSA-N |
Pubchem ID : | 12343539 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 sodium cyanoborohydride; In methanol; diethyl ether; dichloromethane; | EXAMPLE 1 4-[2-(2-Phenylmorpholino)propyl]phenoxyacetic acid methyl ester hydrochloride A mixture of 2-phenylmorpholine hydrochloride (6.05 g), 1-(4-carbomethoxymethoxyphenyl)propan-2-one (6.63 g) and sodium cyanoborohydride (1.61 g) in methanol (100 ml) was stirred at room temperature for 22 hours. The solvent was removed under reduced pressure and aqueous sodium bicarbonate solution added to the residue and extracted with dichloromethane (*2). The extracts were washed with aqueous sodium bicarbonate, dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated to dryness to give an oil. Chromatography on silica gel in 0→7% methanol in dichloromethane gave an oil which was dissolved in diethyl ether and treated with an ethereal solution of hydrogen chloride. Evaporation to dryness and trituration of the residue with ethyl acetate gave a solid. Recrystallisation of this solid gave the title compound, m.p. 187-190 C. (methanol-ethyl acetate), of analytical purity. 1 H nmr δ(DMSO-d6). 1.15 (3H,d), 2.6-3.65 (7H,m), 3.70 (3H,s), 4.2 (2H,m), 4.75 (2H,s), 5.15 (1H,d), 6.9 (2H,d), 7.25 (2H,d), 7.3-7.6 (5H,m), 12.0 (1H, broad; exchanges with D2 O). The mother liquors from the above crystallisation were evaporated to dryness and subsequently used in Example 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With MP-triacetoxyborohydride; In tetrahydrofuran; at 20.0℃; | Example 1 : 2-Phenyl-4-(2'-trifluoromethyI-biphenyl-4-vImethvI)-morpholine; 4-(4-Bromo-benzyl)-2-phenyl morpholine; 429mg of 4-Bromobenzaldehyde was dissolved in 6mL of THF and 386 mg of the HCl salt of 2-Phenylmorpholine (Array) and 1.15g OfMP-BH(OAc)3 (2.77mmol/g) was added. The reaction was agitated on an orbital shaker overnight at room temperature. The reaction was filtered and the resin washed several times with dichloromethane. The filtrate was concentrated and purified by flash chromatography. Yield: 281mg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37.0% | With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 50.0℃;sealed microwave tube; | [00202] Into a 10 ml sealed microwave tube was added 4-bromo-6,7- dimethoxycinnoline (99.9 mg, 0.371 mmol), 2-phenylmorpholine hydrochloride (89.6 mg, 0.449 mmol), tris(dibenzylideneacetone)dipalladium(0) (20.4 mg, 0.0223 mmol), 9,9- dimethyl-4,5-bis(diphenylphosphino)xanthane (22.8 mg, 0.0394 mmol), sodium tert-butoxide (93.8 mg, 0.976 mmol) and toluene (3 mL). The resulting red-brown suspension was stirred at 50 0C overnight, and then filtered through celite, which was washed with ethyl acetate (20 mL). The combined organics were concentrated, and the crude product was purified by column chromatography (using a gradient elution of 20-80% acetonitrile: water with 0.1% formic acid and a flow rate of 45 mL/min). The organic layer was loaded onto an SCX column (1.0 g). The SCX column was rinsed once with two column volumes of methanol and the product was eluted using 7.0 M ammonia in methanol (8 mL). Volatiles were removed in vacuo to afford 48.3 mg of 6,7-dimethoxy-4-(2-phenylmorpholin-4-yl)cinnoline (37.0 % yield). 1H NMR (CDCl3) d 8.81 (s, 1 H), 7.71 (s, 1 H), 7.40 (m, 5 H), 7.17 (s, 1 H), 4.88 (d, J = 9.0 Hz, 1 H), 4.28 (d, J = 12.0 Hz, 1 H), 4.17 (d, J = 12.0 Hz, 1 H), 4.09 (s, 6 H), 3.64 (d, J = 12.0 Hz, 1 H), 3.52 (d, J = 12.0 Hz, 1 H), 3.29 (t, J = 10.5 Hz, 1 H), 3.07 (t, J = 12.0 Hz, 1 H). LC/MS (EI) tR 4.2 min (Method B), m/z 352.1 (M++.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 50.0℃; | Example 12; Synthesis of 7-methoxy-6-(2-methoxyethoxy)-4-(2-phenylmoφholin-4-yl)cinnoline; [00256] Into a 10 ml sealed microwave tube is added 4-bromo-7-methoxy-6-(2- methoxyethoxy)cinnoline (0.371 mmol), 2-phenylmorpholine hydrochloride (89.6 mg, 0.449 mmol), tris(dibenzylideneacetone)dipalladium(0) (20.4 mg, 0.0223 mmol), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthane (22.8 mg, 0.0394 mmol), sodium tert-butoxide (93.8 mg, <n="64"/>0.976 mmol) and toluene (3 mL). The resulting suspension is stirred at 50 0C, and then filtered through celite, which is washed with ethyl acetate. The combined organics are concentrated, and the crude product is purified by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With triethylamine; HATU; In acetonitrile; at 20.0℃; for 16.0h; | i) (4-Amino-phenyl)-(2-phenyl-morpholin-4-yl)-methanoneTo a stirred suspension of benzoic acid (160mg, lmmol) and 2-phenylmorpholine hydrochloride (300mg, 1.5mmol) in acetonitrile (10ml) was added triethylamine (0.4ml, 3mmol) followed by HATU and the reaction mixture was stirred at room temperature for 16 hours. The reaction was diluted with dichloromethane (25ml) and washed with sodium hydrogen carbonate (25ml, saturated solution). The organics were collected, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with ethylacetate to afford the title compound as a clear oil (240mg, 84% yield). HPLC retention time 5.05min. Mass spectrum (ES+) m/z 283 (M+H). |
Tags: 23972-42-1 synthesis path| 23972-42-1 SDS| 23972-42-1 COA| 23972-42-1 purity| 23972-42-1 application| 23972-42-1 NMR| 23972-42-1 COA| 23972-42-1 structure
A757362 [1432794-08-5]
(S)-2-Phenylmorpholine hydrochloride
Similarity: 1.00
A481395 [1186384-50-8]
(2S,6S)-2,6-Diphenylmorpholine
Similarity: 0.98
A757362 [1432794-08-5]
(S)-2-Phenylmorpholine hydrochloride
Similarity: 1.00
A481395 [1186384-50-8]
(2S,6S)-2,6-Diphenylmorpholine
Similarity: 0.98
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