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Morpholine → 4-[3-(2-Methoxyethoxy)-5-nitrophenyl]morpholine

HRID 185
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HRID 185 반응식
C1COCCN1.COCCOc1cc(I)cc([N+](=O)[O-])c1>CC(=O)O.CC(=O)O.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COCCOc1cc(N2CCOCC2)cc([N+](=O)[O-])c1
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참가 물질

7

반응물 2

HCID 8083MorpholineHCID 598178111-Iodo-3-(2-methoxyethoxy)-5-nitro-benzene

생성물 1

HCID 598178384-[3-(2-Methoxyethoxy)-5-nitrophenyl]morpholine수율 16.14%

시약·촉매·용매 4

HCID 10796Cesium carbonate시약HCID 634876Binap, (A+-)-촉매
HCID 4144353
Palladium (II) acetate
촉매
HCID 1140Toluene용매

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온도
110 °C

실험 절차

diacetoxypalladium (0.136 g, 0.60 mmol) was added to a stirred mixture of 1-iodo-3-(2-methoxyethoxy)-5-nitrobenzene (3.9 g, 12.07 mmol), morpholine (1.373 mL, 15.69 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.225 g, 0.36 mmol) and cesium carbonate (11.80 g, 36.21 mmol) dissolved in toluene (100 mL) over a period of 5 minutes, degased and under argon. The resulting mixture was heated at 110 °C for 4 hours.The toluene was evaporated , water ( 50ml) was added and the mixture was extracted with ethyle acetate, dried over MgSO4, filtered and asorbed on silica gel.The crude product was purified by flash chromatography on silica gel eluting with 1 to 4% methanol in dichloromethane. The solvent was evaporated to dryness to afford 4-(3-(2-methoxyethoxy)-5-nitrophenyl)morpholine (0.550 g, 16.14 %) as a orange solid. ( starting material unreacted : 2 .5g)

출처 및 근거

ORD 기록
ord-5a683960052443b49da1956ac277ce2a
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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