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

HRID 375535Notes

Reaction equation

HRID 375535 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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%

Sources & evidence

ORD record
ord-0a202009b66243b29e703b8e6f171c06
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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