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tert-Butyl piperazine-1-carboxylate → N-(4-methoxy-3-piperazin-1-yl-phenyl)-acetamide

HRID 521
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HRID 521 반응식
CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(NC(C)=O)cc1Br>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.[Na+].[Pd]>COc1ccc(NC(C)=O)cc1N1CCNCC1
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7

반응물 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 244158N-(3-bromo-4-methoxyphenyl)acetamide

생성물 1

HCID 82480614N-(4-methoxy-3-piperazin-1-yl-phenyl)-acetamide수율 50.91%

시약·촉매·용매 4

HCID 23676156Sodium t-butoxide시약HCID 4144353Palladium (II) acetate촉매
HCID 16217985
2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl
촉매
HCID 1140Toluene용매

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온도
100 °C

실험 절차

A solution of N-(3-bromo-4-methoxyphenyl)acetamide (0.5 g, 2.05 mmol) dissolved in toluene (5 mL) was treated with tert-butyl piperazine-1-carboxylate (0.382 g, 2.05 mmol), diacetoxypalladium (0.046 g, 0.20 mmol), dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine (0.191 g, 0.41 mmol) and sodium 2-methylpropan-2-olate (0.433 g, 4.51 mmol) in a sealed tube. The resulting mixture was degassed and stirred at 100 °C for 8 hours in a microwave. The mixture was pre-absorbed onto silica. The crude product was purified by flash silica chromatography, elution 50% ethyl acetate in Heptane. Pure fractions were evaporated to dryness to afford intermediate. The intermediate was dissolved in 4M HCl in dioxane (10mL) and stirred at RT overnight. The mixture was evaporated to give N-(4-methoxy-3-(piperazin-1-yl)phenyl)acetamide (0.260 g, 50.9 %) as a tan solid.

출처 및 근거

ORD 기록
ord-d3fce1c8e3204b57a80e5c0d53c5c1f7
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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