N-(3-benzhydroxypropyl)piperazine → N-[3-[3,5-dimethoxy-4-(beta-methoxyethoxymethoxy) phenyl]-2-propenoyl]-N'-(3-benzhydroxypropyl)piperazine

HRID 652967Notes

Reaction equation

HRID 652967 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.CON1C([C:38](=[O:58])[CH:39]=[CH:40][C:41]2[CH:46]=[C:45]([O:47][CH3:48])[C:44]([O:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH3:55])=[C:43]([O:56][CH3:57])[CH:42]=2)(OCOCCOC)C(OC)SC1=S>O1CCCC1>[CH3:48][O:47][C:45]1[CH:46]=[C:41]([CH:40]=[CH:39][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:58])[CH:42]=[C:43]([O:56][CH3:57])[C:44]=1[O:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH3:55]

Participants

4

Reactant 2

HCID 22110970N-(3-benzhydroxypropyl)piperazineHCID 867416223,5-Dimethoxy-4-(beta-methoxyethoxymethoxy) (3,5-dimethoxy-4(beta-methoxyethoxymethoxy) phenyl-2-propenoyl]thiazolidine-2-thione

Product 1

HCID 53774023N-[3-[3,5-dimethoxy-4-(beta-methoxyethoxymethoxy) phenyl]-2-propenoyl]-N'-(3-benzhydroxypropyl)piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 160 mg (0.52 mmol) of N-(3-benzhydroxypropyl) piperazine in dry tetrahydrofuran (5 ml) was added a solution of 206 mg (0.5 mmol) of N-[3-(3,5-dimethoxy-4-(β-methoxyethoxymethoxy) (3,5-dimethoxy-4(β-methoxyethoxymethoxy) phenyl-2-propenoyl]thiazolidine-2-thione in dry tetrahydrofuran, and the mixture was allowed to react at room temperature overnitht. 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 270 mg (0.45 mmol) of N-[3-[3,5-dimethoxy-4-(β-methoxyethoxymethoxy) phenyl]-2-propenoyl]-N'-(3-benzhydroxypropyl)piperazine.

Workup

  1. customto react at room temperature overnitht
  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 chloroform - methanol (50 : 1)

Sources & evidence

ORD record
ord-5db78b2a04c8442b8377ced29509adb1
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

Loading…