40299-87-4|2-Bromo-1-morpholinoethanone| Ambeed

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Quality Control of [ 40299-87-4 ] Purity: 97% SDS Specification

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Product Details of [ 40299-87-4 ]

CAS No. :	40299-87-4
Formula :	C₆H₁₀BrNO₂
M.W :	208.05
SMILES Code :	BrCC(=O)N1CCOCC1
MDL No. :	MFCD06800306
InChI Key :	LLLQAMNGYJQUKK-UHFFFAOYSA-N
Pubchem ID :	13996876

Safety of [ 40299-87-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 40299-87-4 ]

* 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.

Downstream synthetic route of [ 40299-87-4 ]

[ 40299-87-4 ] Synthesis Path-Downstream 1~36

1
[ 40299-87-4 ]
[ 14538-16-0 ]
[ 38922-43-9 ]
[ 23599-20-4 ]

References: [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 951 - 954.

2
[ 40299-87-4 ]
[ 139-94-6 ]
[ 52121-26-3 ]

References: [1]Journal of Medicinal Chemistry,1974,vol. 17,p. 207 - 209.

3
[ 110-91-8 ]
[ 598-21-0 ]
[ 40299-87-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	In dichloromethane; at 0 - 20℃; for 1.5h;Inert atmosphere;	General procedure: Amine (2.0 equiv.) was added to stirred solution of bromoacetyl bromide (1.0 equiv.) in DCM (ca. 0.15 M) at 0 C. After 30 min, reaction was warmed to rt, stirred for 1 h, and saturated ammonium chloride solution was added. The mixture was extracted with Et2O (2 x), dried over anhydrous Na2SO4, filtered, and concentrated to dryness.
62%	With N-ethyl-N,N-diisopropylamine; In dichloromethane;	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 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) delta 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 - 20℃; for 0.75h;	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 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) delta 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 - 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.

References: [1]Tetrahedron Letters,2011,vol. 52,p. 3714 - 3717.
[2]Organic Letters,2017,vol. 19,p. 2338 - 2341.
[3]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1407 - 1413.
[4]Biopolymers,2016,p. 726 - 736.
[5]Green Chemistry,2014,vol. 16,p. 2252 - 2265.
[6]Organic Letters,2011,vol. 13,p. 3138 - 3141.
[7]ACS Combinatorial Science,2012,vol. 14,p. 280 - 284.
[8]Tetrahedron Letters,2009,vol. 50,p. 5689 - 5691.
[9]Patent: US2004/102636,2004,A1 .
[10]Patent: US2008/269265,2008,A1 .Location in patent: Page/Page column 12.
[11]Patent: EP1449834,2004,A2 .Location in patent: Page 19.
[12]Patent: EP1042305,2005,B1 .Location in patent: Page/Page column 24-25.
[13]Journal of Medicinal Chemistry,1992,vol. 35,p. 1685 - 1701.
[14]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1122 - 1126.
[15]Chemistry - A European Journal,2013,vol. 19,p. 18011 - 18026.
[16]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4174 - 4177.
[17]Patent: WO2006/86449,2006,A2 .Location in patent: Page/Page column 93-94.
[18]Patent: US2002/52343,2002,A1 .
[19]Patent: US5382585,1995,A .
[20]Patent: WO2006/86633,2006,A2 .Location in patent: Page/Page column 65.
[21]Chemistry - A European Journal,2009,vol. 15,p. 4538 - 4542.
[22]Tetrahedron,2009,vol. 65,p. 6128 - 6134.
[23]Tetrahedron,2012,vol. 68,p. 4710 - 4718.
[24]Chemistry of Natural Compounds,2013,vol. 48,p. 1047 - 1053.
Khim. Prir. Soedin.,2012,vol. 48,p. 924 - 929,6.
[25]Green Chemistry,2013,vol. 15,p. 2727 - 2739.
[26]Patent: WO2014/159251,2014,A2 .Location in patent: Page/Page column 132.
[27]Journal of Organic Chemistry,2015,vol. 80,p. 8922 - 8928.
[28]Patent: US2017/298090,2017,A1 .Location in patent: Paragraph 0141; 0142.
[29]Patent: WO2005/32484,2005,A2 .Location in patent: Page/Page column 118-119.
[30]Patent: WO2019/7696,2019,A1 .Location in patent: Paragraph 0255.
[31]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 2839 - 2852.
[32]Journal of Heterocyclic Chemistry,2020.

4
[ 40299-87-4 ]
[ 117953-08-9 ]
[ 137184-92-0 ]

References: [1]Synthetic Communications,1991,vol. 21,p. 1991 - 1998.

5
[ 40299-87-4 ]
[ 138498-62-1 ]
[ 138484-07-8 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1685 - 1701.

6
[ 40299-87-4 ]
demethyl A₂ [ No CAS ]
2C₆₀H₉₁N₁₈O₂₃S₃⁽¹⁺⁾*O₄S^(2-) [ No CAS ]

References: [1]Heterocycles,1984,vol. 22,p. 779 - 783.

7
[ 226911-47-3 ]
[ 40299-87-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-3-Methyl-4-{(E)-2-[6-(2-morpholin-4-yl-2-oxo-ethoxy)-quinolin-2-yl]-vinyl}-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1544 - 1548.

8
[ 149747-23-9 ]
[ 40299-87-4 ]
2-(5-methyl-4-<i>p</i>-tolyl-4<i>H</i>-[1,2,4]triazol-3-ylsulfanyl)-1-morpholin-4-yl-ethanone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4174 - 4177.

9
[ 40299-87-4 ]
[ 174150-18-6 ]
C₁₈H₃₂NO₃S⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 2105 - 2114.

10
[ 40299-87-4 ]
1-[(2S,3S,5R)-2-carboxy-3-methyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]hept-3-yl]methyl}-3-(2-morpholin-4-yl-2-oxoethyl)-1H-1,2,3-triazol-3-ium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of (2S,3S,5R)-3-methyl-7-oxo-3-(/No.-l,2,3-tnazol-l- ylmethyl)-4-thia-l-azabicyclo-[3.2.0]heptane-2-carboxylic acid 4,4-dioxide (10 g) in dimethylformamide (100 mL) was added N,O-bis(silylacetamide) (10 g) and stirred for 30 min. at 25 to 30C. To the clear solution was added 4- (bromoacetyl)morpholine (14 g) during 20 min. at 25-30 0C under stirring. The reaction mixture was heated to 50 C and stirred at the same temperature for 3 days. Diisopropylether (300 mL) was added to the reaction mixture at 25-30 C and stirred for 1 h. The precipitated mass was separated out and dissolved purified water (100 mL). <n="19"/>Dichloromethane (100 niL) aws added to the resultant clear solution, and stirred for 1 h at 10 to 15 C and the organic layer separated. The aqueous layer was washed with freshly prepared solution of Amberlite LA-2 resin twice, followed by dichloromethane wash. To the aqueous solution, activated carbon (1 g) was added, stirred for 15 min., filtered and washed with purified water (25 mL). The solution was filtered and lyophilized to get the title compound (7 g). The crude product (0.5 g) was purified to obtain the pure title product (0.3 g). 1H NMR (400 MHz, DMSO) Jppm: 1.36 (s, 3H), 3.15 (d, J = 16.0 Hz, IH), 3.43 - 3.67 (m, 9H), 3.97 (s, IH), 5.06 (d, J = 4.1 Hz, IH), 5.37 (d, J = 14.8 Hz, IH), 5.49 (d, J = 14.8 Hz, IH), 5.94 (s, 2H), 8.87 (s, IH), 8.97 (s, IH). Mass m/z: M+l peak at 428.
		To a suspension of (2S,3S,5R)-3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylic acid 4,4-dioxide (10 g) in dimethylformamide (100 mL) was added N,O-bis(silylacetamide) (10 g) and stirred for 30 min. at 25 to 30 C. To the clear solution was added 4-(bromoacetyl)morpholine (14 g) during 20 min. at 25-30 C. under stirring. The reaction mixture was heated to 50 C. and stirred at the same temperature for 3 days. Diisopropylether (300 mL) was added to the reaction mixture at 25-30 C. and stirred for 1 h. The precipitated mass was separated out and dissolved purified water (100 mL). Dichloromethane (100 mL) aws added to the resultant clear solution, and stirred for 1 h at 10 to 15 C. and the organic layer separated. The aqueous layer was washed with freshly prepared solution of Amberlite LA-2 resin twice, followed by dichloromethane wash. To the aqueous solution, activated carbon (1 g) was added, stirred for 15 min., filtered and washed with purified water (25 mL). The solution was filtered and lyophilized to get the title compound (7 g). The crude product (0.5 g) was purified to obtain the pure title product (0.3 g). 1H NMR (400 MHz, DMSO) delta ppm: 1.36 (s, 3H), 3.15 (d, J=16.0 Hz, 1H), 3.43-3.67 (m, 9H), 3.97 (s, 1H), 5.06 (d, J=4.1 Hz, 1H), 5.37 (d, J=14.8 Hz, 1H), 5.49 (d, J=14.8 Hz, 1H), 5.94 (s, 2H), 8.87 (s, 1H), 8.97 (s, 1H). Mass m/z: M+1 peak at 428.

References: [1]Patent: WO2008/10048,2008,A2 .Location in patent: Page/Page column 17-18.
[2]Patent: US2008/15156,2008,A1 .Location in patent: Page/Page column 7.

11
[ 40299-87-4 ]
[ 2058-74-4 ]
1-methyl-3'-(morpholin-4-ylcarbonyl)spiro[indole-3,2'-oxiran]-2(1H)-one [ No CAS ]
1-methyl-3'-(morpholin-4-ylcarbonyl)spiro[indole-3,2'-oxiran]-2(1H)-one [ No CAS ]

References: [1]Organic Letters,2007,vol. 9,p. 1745 - 1748.

12
C₁₈H₂₃NO₃ [ No CAS ]
[ 40299-87-4 ]
C₂₄H₃₂N₂O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2465 - 2469.

13
[ 110-91-8 ]
[ 13094-51-4 ]
[ 40299-87-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2465 - 2469.

14
[ 40299-87-4 ]
3-Morpholin-4-yl-2H-benzo[1,4]thiazine 1,1-dioxide [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 347 - 350.

15
[ 40299-87-4 ]
[ 178674-95-8 ]

References: [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 347 - 350.

16
[ 40299-87-4 ]
(1,1-Dioxo-1,4-dihydro-1λ⁶-benzo[1,4]thiazin-2-yl)-morpholin-4-yl-methanone [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 347 - 350.

17
[ 40299-87-4 ]
4-(2-{2-Methyl-5-propyl-4-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-2H-pyrazol-3-yloxy}-ethyl)-morpholine [ No CAS ]