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

HRID 2241268

反応式

HRID 2241268 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-569affb3dc5d46d68f3789f3aab2719a
出典データセット
uspto-grants-2010_05
特許番号
US07723330B2

関連ノート

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