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

HRID 375535노트

반응식

HRID 375535 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-0a202009b66243b29e703b8e6f171c06
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05486517

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