Triethylamine → 4-[4-(4-Phenylpiperazin-1-yl)but-1-ynyl]benzaldehyde

HRID 375535ノート

反応式

HRID 375535 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)[CH2:11][C:12]#[CH:13].C(N(CC)CC)C>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:20]1([N:17]2[CH2:16][CH2:15][N:14]([CH2:10][CH2:11][C:12]#[C:13][C:2]3[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=3)[CH2:19][CH2:18]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 707414-BromobenzaldehydeHCID 189930381-(But-3-yn-1-yl)-4-phenylpiperazine

生成物 1

HCID 189930464-[4-(4-Phenylpiperazin-1-yl)but-1-ynyl]benzaldehyde収率 60.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4-bromobenzaldehyde (4.05 g), 1-but-3-ynyl-4-phenylpiperazine (Step A) (4.69 g), triethylamine (9.2 mL), bis (triphenylphosphine)palladium dichloride (0.31 g) and copper (I) iodide (0.08 g) in acetonitrile (100 mL) is degassed with nitrogen and stirred at room temperature for 16 hours. The solvent is evaporated and the residue is dissolved in dichloromethane (200 mL), washed with 2N sodium carbonate (150 mL), dried over MgSO4, filtered and evaporated to leave a brown oil. This oil is purified by MPLC on silica gel eluting with 15% then 30% ethyl acetate (EtOAc)/hexanes to give 4.2 g of the title compound as a yellow waxy solid.

後処理

  1. customis degassed with nitrogen
  2. customThe solvent is evaporated
  3. dissolutionthe residue is dissolved in dichloromethane (200 mL)
  4. washwashed with 2N sodium carbonate (150 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a brown oil
  9. customThis oil is purified by MPLC on silica gel eluting with 15%

出典と根拠

ORDレコード
ord-0a202009b66243b29e703b8e6f171c06
出典データセット
uspto-grants-1996_01
特許番号
US05486517

反応ノート

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