| 62% |
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 0.75h; |
To an ice cold solution of morpholine (2.17 g, 24.9 mmol) and diisopropylethylamine (3.21 g, 24.9 mmol) in CH2Cl2 (70 mL) was added a solution of bromoacetyl bromide (5.05 g, 25 mmole) in CH2Cl2 (8 mL) via syringe. The resulting solution was kept at 0 C for 45 min, then was allowed to warm to room temp. The reaction mixture was diluted with EtOAc (500 mL), sequentially washed with a 1M HCl solution (250 mL) and a saturated NaCl solution (250 mL), and dried (MgSO4) to give the desired product (3.2 g, 62%): 1H-NMR (DMSO-d6) ? 3.40-3.50 (m, 4H), 3.50-3.60 (m, 4H), 4.11 (s, 2H). |
| 62% |
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 0.75h; |
A9. General Method for Synthesis of Aryl Anilines via Alkylation of a Nitrophenol Followed by Reduction; [] Step 1.4-(alpha-Bromoacetyl)morpholine: To an ice cold solution of morpholine (2.17 g, 24.9 mmol) and diisopropylethylamine (3.21 g, 24.9 mmol) in CH2Cl2 (70 mL) was added a solution of bromoacetyl bromide (5.05 g, 25 nunole) in CH2Cl2 (8 mL) via syringe. The resulting solution was kept at 0 C for 45 min, then was allowed to warm to room temp. The reaction mixture was diluted with EtOAc (500 mL), sequentially washed with a 1M HCl solution (250 mL) and a saturated NaCl solution (250 mL), and dried (MgSO4) to give the desired product (3.2 g, 62%): 1H-NMR (DMSO-d6) delta 3.40-3.50 (m, 4H), 3.50-3.60 (m, 4H), 4.11 (s, 2H). |
| 54% |
With triethylamine; In dichloromethane; at -4℃; for 1.5h;Inert atmosphere; |
Morpholine (9.9 mmoles, 0.87 mL) wasdissolved in CH2Cl2 (0.2 M, 50 mL), Et3N (0.015 moles, 2.07 mL, 1.5 equiv) was added and the mixture was cooled to -4 C. Bromoacetyl bromide (9.9mmoles, 0.86 mL, 1.0 equiv) was then added dropwise and the reaction was allowed to stir at thesame temperature for 1.5 h. The reaction mixture was washed with saturated NH4Cl (2x30 mL)and saturated NaHCO3 (2x30 mL) and then concentrated to dryness. Purification by flashcolumn chromatography (50?80% EtOAc / Hexanes) furnished 1.12 g of the desiredmorpholinoacetyl bromide 27 in 54% yield (un-optimized); |
|
In dichloromethane; at -25℃; for 1.25h; |
A solution of bromoacetyl bromide (3.0 mL, 0.034 mol) in dichloromethane (240 mL) was cooled to -25 C. A solution of morpholine (9.0 mL, 0.10 mol) in dichloromethane (20 mL) was slowly added over a period of one hour. After the addition was complete, the reaction was stirred at -25 C for 15 minutes and allowed to warm to ambient temperature. Dichloromethane was added, and the resulting solution was washed with water, IN aqueous hydrogen chloride, and brine; dried over magnesium sulfate; EPO <DP n="95"/>filtered; and concentrated under reduced pressure to provide 4-(bromoacetyl)morpholine as a colorless oil. |
|
With triethylamine; |
3-Hydroxy-7-(2-morpholin-4-yl-2-oxo-ethoxy)-naphthalene-2-carboxylic acid benzyl ester A mixture of morpholine (2.16 mL, 25 mmol) and anhydrous ether (30 mL) was cooled (-10 C.) and treated drop wise with a solution of bromoacetyl bromide (5.0 g, 25 mmol) in ether (20 mL). Triethyl amine (3.5 mL, 25 mmol) then was added drop wise to the reaction mixture to form a cream colored reaction mixture. The creamy reaction mixture was agitated at about 20 C. for about 6 hours. The reaction solids were isolated and rinsed with ether. The combined ether fractions were concentrated under reduced pressure to afford N-(2-bromoacetyl)-morpholine (3.37 g) as a reddish oil, which was used without further purification. |
|
In tetrahydrofuran; |
a) 50 g (0.57 mol) of morpholine are added dropwise at 10 C. to a solution of 58 g (0.28 mol) of bromoacetyl bromide in 500 ml THF. After 2 hours, precipitated morpholine hydrobromide is filtered off, the filtrate is concentrated and the residue is distilled in vacuo at 110 C./0.5 mm Hg. 39 g (67%) of bromoacetyl morpholide are obtained as colourless crystals which melt a little above room temperature. |
|
In dichloromethane; at -25℃; for 1.25h; |
A solution of bromoacetyl bromide (3.0 mL, 0.034 mol) in dichloromethane (240 mL) was cooled to -25 0C. A solution of morpholine (9.0 mL, 0.10 mol) in dichloromethane (20 mL) was slowly added over a period of one hour. After the addition was complete, the reaction was stirred at -25 C for 15 minutes and then allowed to warm to ambient temperature. Dichloromethane was added, and the resulting solution was washed sequentially with water, IN aqueous hydrogen chloride, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure to provide 4- (bromoacetyl)morpholine as a colorless oil |
|
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 1.5h;Inert atmosphere; |
General procedure: A solution of diethylamine (0.72 mL, 7.0 mmol) and N,N-diisopropylethylamine (1.22 mL, 7.0 mmol) in dichloromethane (23 mL) was treated with bromoacetyl bromide (0.61 mL, 7.0 mmol) at 0 C. The mixture was stirred for 1.5 h at the same temperature and diluted with water. Extractive workup and evaporation of the volatiles gave N,N-diethyl-2-bromoacetamide (20) (1.17 g, 86% yield) as a yellow oil. The following procedure was the same with that of 4d(84% overall yield from 20). |
|
In dichloromethane; at 0℃; for 1.5h; |
Compound No. 23a was prepared by dissolving 2-bromoacetyl bromide (0.861 mL, 9.91 mmol) in dichloromethane (100 mL) at 0C, at which point morpholine (1.726 g, 19.82 mmol) in dichloromethane (12 mL) was added slowly at 0 C and stirred for 90 minutes. The reaction mixture was washed with water twice, dried through magnesium sulfate, and concentrated to give 2-bromo-l -morpholinoethanone as a pale-yellow liquid as the desired product. NMR spectroscopy was consistent with the proposed structure. |
|
With triethylamine; In dichloromethane; at 20℃; for 1h; |
To a solution of 2-bromoacetyl bromide (2.3 g, 11.4 mmol) in 50 mE DCM was added morpholine (1.22 g, 14 mmol) and Et3N (1.9 mE, 13.7 mmol). The reaction was stirred at room temperature for 1 hr. The mixture was washed with water, brine, dried and concentrated to give crude product used directly. |
|
In dichloromethane; at -25℃; for 1.25h; |
A solution of bromoacetyl bromide (3.0 mL, 0.034 mol) in dichloromethane (240 ML) was cooled TO-25 C. A solution of morpholine (9.0 mL, 0.10 mol) in dichloromethane (20 mL) was slowly added over a period of one hour. After the addition was complete, the reaction was stirred AT-25 C for 15 minutes and allowed to warm to ambient temperature. Dichloromethane was added, and the resulting solution was washed with water, 1N aqueous hydrogen chloride, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure to provide 4- (2-bromoacetyl) morpholine as a colorless oil. |
|
In dichloromethane; at -46 - 20℃; for 1h; |
Morpholine (1.3 mL, 87 mmol, 2 eq) is added dropwise over 15 min to a cooled solution (-46C)of2-bromoacetyl bromide (0.65 mL, 7.4 mmol, 1 eq) in dry DCM (35 mL). After the addition, the reactionmixture is left to warm up to room temperature and stirred for 1 h. The mixture is washed (sat. NH4Cl,NaHC03 and brine), dried (Na2S04) and concentrated to afford the desired product. |
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