1-[2-(Diphenylmethoxy)ethyl]piperazine → N-[3[3,5-dimethoxy-4-(beta-methoxyethoxymethoxy)phenyl]-2-propenoyl]-N'-(2-benzhydroxyethyl) piperazine

HRID 652965Notes

Reaction equation

HRID 652965 reaction equation
[CH:1]([O:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]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.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:40]=[CH:41][C:42](N2CCSC2=S)=[O:43])[CH:28]=[C:29]([O:38][CH3:39])[C:30]=1[O:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37]>CN(C)C=O>[CH3:39][O:38][C:29]1[CH:28]=[C:27]([CH:40]=[CH:41][C:42]([N:20]2[CH2:19][CH2:18][N: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)[CH2:22][CH2:21]2)=[O:43])[CH:26]=[C:25]([O:24][CH3:23])[C:30]=1[O:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37]

Participants

4

Reactant 2

HCID 6485251-[2-(Diphenylmethoxy)ethyl]piperazineHCID 54253413N-[3-[3,5-dimethoxy-4-(beta-methoxyethoxymethoxy) phenyl]-2-propenoyl]thiazolidine-2-thione

Product 1

HCID 53756827N-[3[3,5-dimethoxy-4-(beta-methoxyethoxymethoxy)phenyl]-2-propenoyl]-N'-(2-benzhydroxyethyl) piperazineYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 424 mg (1.43 mmol) of N-(2-benzhydroxyethyl) piperazine in dry dimethylformamide (2 ml) was added 475 mg (1.15 mmol) of N-[3-[3,5-dimethoxy-4-(β-methoxyethoxymethoxy) phenyl]-2-propenoyl]thiazolidine-2-thione, and the mixture was reacted at room temperature for 2 hours under argon atmosphere. The reaction mixture was concentrated by evaporation under reduced pressure and the residue was subjected to silica gel column chromatography, eluted with chloroform-methanol (100 : 1), to give 588 mg (0.995 mmol) of N-[3[3,5-dimethoxy-4-(β-methoxyethoxymethoxy)phenyl]-2-propenoyl]-N'-(2-benzhydroxyethyl) piperazine.

Workup

  1. customthe mixture was reacted at room temperature for 2 hours under argon atmosphere
  2. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  3. washeluted with chloroform-methanol (100 : 1)

Sources & evidence

ORD record
ord-69087b64cc96444ba340a619533d22cd
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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