N-(3-benzhydroxypropyl)piperazine → N-[5-(3,4-dimethoxyphenyl)-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazine

HRID 652972Notes

Reaction equation

HRID 652972 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.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][CH:36]=[CH:37][C:38](N2CCSC2=S)=[O:39])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]>O1CCCC1>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][CH:36]=[CH:37][C:38]([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:39])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]

Participants

4

Reactant 2

HCID 22110970N-(3-benzhydroxypropyl)piperazineHCID 53687665N-[5-(3,4-dimethoxyphenyl)-2,4-pentadienoyl]thiazolidine-2-thione

Product 1

HCID 54030713N-[5-(3,4-dimethoxyphenyl)-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 310 mg (1 mmol) of N-(3-benzhydroxypropyl)piperazine in dry tetrahydrofuran (5 ml) was added a solution of 483 mg (1 mmol) of N-[5-(3,4-dimethoxyphenyl)-2,4-pentadienoyl]thiazolidine-2-thione in dry tetrahydrofuran (5 ml), and the mixture was allowed to react at room temperature for overnight under argon atmosphere. 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 chloroform-methanol (50:1), to give 470 mg (0.89 mmol) of N-[5-(3,4-dimethoxyphenyl)-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazine. Spectrophotometric data of the product support the structure shown below. ##STR107##

Workup

  1. customto react at room temperature for overnight under argon atmosphere
  2. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  3. additiondiluted with chloroform
  4. washwashed
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. washeluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-f7c6c1ab16c54a459e3831d21ac17fcb
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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