N-(3-benzhydroxypropyl)piperazine → N-[3-[3-methoxy-4-(beta-methoxyethoxymetoxy) phenyl]-2-propenoyl]-N'-(3-benzhydroxypropyl)-piperazine

HRID 652963Notes

Reaction equation

HRID 652963 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:39]=[CH:40][C:41](N2CCSC2=S)=[O:42])[CH:29]=[CH:30][C:31]=1[O:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38]>O1CCCC1>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:39]=[CH:40][C:41]([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:42])[CH:29]=[CH:30][C:31]=1[O:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38]

Participants

4

Reactant 2

HCID 22110970N-(3-benzhydroxypropyl)piperazineHCID 54567004N-[3-[3-methoxy-4-(beta-methoxyethoxymethoxy)phenyl]-2-propenoyl) thiazolidine-2-thione

Product 1

HCID 70436154N-[3-[3-methoxy-4-(beta-methoxyethoxymetoxy) phenyl]-2-propenoyl]-N'-(3-benzhydroxypropyl)-piperazineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 620 mg (2 mmol) of the piperazine derivative in dry tetrahydrofuran (5 ml) was added a solution of 766 mg (2.0 mmol) of N-[3-[3-methoxy-4-(β-methoxyethoxymethoxy)phenyl]-2-propenoyl) thiazolidine-2-thione in dry tetrahydrofuran (5 ml), and the mixture was allowed to react at room temperature overnight under argon atmosphere. The reaction mixture was concentrated by evaporation under reduced pressure, diluted with N'chloroform and washed, in turn, with 2N aqueous solution of sodium hydroxide and water. The organic layer was dried over anhydrous scdium 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 1.08 g (1.88 mmol) of N-[3-[3-methoxy-4-(β-methoxyethoxymetoxy) phenyl]-2-propenoyl]-N'-(3-benzhydroxypropyl)-piperazine.

Workup

  1. customto react at room temperature overnight under argon atmosphere
  2. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  3. additiondiluted with N'chloroform
  4. washwashed, in turn, with 2N aqueous solution of sodium hydroxide and water
  5. dry with materialThe organic layer was dried over anhydrous scdium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. washeluted with chloroform - methanol ((50 : 1)

Sources & evidence

ORD record
ord-034e7122f6f54235b50c5eb416d76ed1
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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