HCID 13754709, compound → HCID 54343586, compound

HRID 652977Notes

Reaction equation

HRID 652977 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)([O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:42]=[CH:43][CH:44]=[CH:45][C:46](N2CCSC2)=[O:47])[CH:30]=[C:31]([O:40][CH3:41])[C:32]=1[O:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH3:39]>CN(C)C=O>[CH3:41][O:40][C:31]1[CH:30]=[C:29]([CH:42]=[CH:43][CH:44]=[CH:45][C:46]([N:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][O:9][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[CH3:8])[CH2:17][CH2:16]2)=[O:47])[CH:28]=[C:27]([O:26][CH3:25])[C:32]=1[O:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH3:39]

Participants

4

Reactant 2

HCID 13754709HCID 13754709, compoundHCID 53901538HCID 53901538, compound

Product 1

HCID 54343586HCID 54343586, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 527 mg (1.53 mmol) of N-[2-[1-phenyl-1-(p-chlorophenyl)ethoxy]ethyl]piperazine in dry dimethylformamide (10 ml) was added, under argon atmosphere, 760 mg (1.73 mmol) of N-[5-[3,5-dimethoxy-4-(β-methoxyethoxymethoxy)phenyl]-2,4-pentadienoyl]thiazolidine, and the mixture was allowed to react at room temperature for 67 hours. 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 618 mg (0.929 mmol) of N-[5-[3,5-dimethoxy-4-(β-methoxyethoxymethoxy)phenyl]-2,4-pentadienoyl]-N'-[2-[1-phenyl-1-(p-chlorophenyl)ethoxy]ethyl]piperazine.

Workup

  1. customto react at room temperature for 67 hours
  2. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  3. washeluted with chloroform-methanol (100:1)

Sources & evidence

ORD record
ord-f749bb1bfdf5428c90338a6fe5ce593a
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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