Acetic Acid → 1-((4-Bromofuran-2-yl)methyl)-4-methylpiperazine

HRID 2241268

반응식

HRID 2241268 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[O:5][CH:6]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[OH-].[Na+]>O.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)[O:5][CH:6]=1

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 27570104-Bromo-2-furaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 160991801-((4-Bromofuran-2-yl)methyl)-4-methylpiperazine

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred mixture of 4-bromofuran-2-carbaldehyde (2.10 g, 12.0 mmol) and THF (10 mL) that was cooled in an ice bath was added 1-methylpiperazine (1.60 ml, 14.4 mmol) dropwise, followed by sodium triacetoxyborohydride (3.81 g, 18.0 mmol) in 3 portions as solid. Acetic acid (0.343 ml, 6.00 mmol) was added, and the reaction was stirred for 18 hours at ambient temperature. The dark mixture was diluted with water (10 mL) and basified to pH>12 by addition of 5N NaOH. The mixture was extracted with diethyl ether (3×50 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated in vacuo. The resulting black oil (2.10 g, 66%) was carried forward without purification.

후처리

  1. temperaturewas cooled in an ice bath
  2. extractionThe mixture was extracted with diethyl ether (3×50 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting black oil (2.10 g, 66%) was carried forward without purification

출처 및 근거

ORD 기록
ord-569affb3dc5d46d68f3789f3aab2719a
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723330B2

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