N-(3-benzhydroxypropyl)piperazine → N-[5-[3,4-di(beta-methoxyethoxy)phenyl)-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazine

HRID 652970Notes

Reaction equation

HRID 652970 reaction equation
[CH:1]([O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCO[CH2:29][O:30][C:31]1[CH:32]=[C:33]([CH:44]=[CH:45][CH:46]=[CH:47][C:48](N2CCSC2=S)=[O:49])[CH:34]=[CH:35][C:36]=1[O:37][CH2:38]OCCOC>O1CCCC1>[CH3:29][O:30][CH2:31][CH2:29][O:30][C:31]1[CH:32]=[C:33]([CH:44]=[CH:45][CH:46]=[CH:47][C:48]([N:21]2[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][O:14][CH:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:19][CH2:20]2)=[O:49])[CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH2:36][O:37][CH3:38]

Participants

4

Reactant 2

HCID 22110970N-(3-benzhydroxypropyl)piperazineHCID 54009022N-[5-[3,4-di(beta-methoxyethoxymethoxy)phenyl]2,4-pentadienoyl]thiazolidine-2-thione

Product 1

HCID 86741623N-[5-[3,4-di(beta-methoxyethoxy)phenyl)-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazineYield 160%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 650 mg (1.2 mmol) of N-(3-benzhydroxypropyl)piperazine in dry tetrahydrofuran (5 ml) was added a solution of 966 mg (2.0 mmol) of N-[5-[3,4-di(β-methoxyethoxymethoxy)phenyl]2,4-pentadienoyl]thiazolidine-2-thione in dry tetrahydrofuran (6 ml), and the mixture was reacted at room temperature for 14 hours. The reaction mixture was concentrated by evaporation under reduced pressure, diluted with chloroform and washed, in turn, with 2N aqueous solution of sodium hydroxide and water. The organic layer was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with 1% methanol in chloroform, to give 1.09 g (1.6 mmol) of N-[5-[3,4-di(β-methoxyethoxy)phenyl)-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazine.

Workup

  1. customthe mixture was reacted at room temperature for 14 hours
  2. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  3. additiondiluted with chloroform
  4. washwashed, in turn, with 2N aqueous solution of sodium hydroxide and water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. washeluted with 1% methanol in chloroform

Sources & evidence

ORD record
ord-277f7cbccc2349f5bf2662ecff3387d9
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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