Water → HCID 18546861, compound

HRID 1267668Notes

Reaction equation

HRID 1267668 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([CH2:19][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(=O)([O-])O.[Na+].[CH3:31][O:32][C:33]1[CH:34]=[C:35]([C:43]2[CH:51]=[CH:50][C:46]([C:47](Cl)=[O:48])=[CH:45][CH:44]=2)[CH:36]=[C:37]([O:41][CH3:42])[C:38]=1[O:39][CH3:40].O>ClCCl>[CH3:31][O:32][C:33]1[CH:34]=[C:35]([C:43]2[CH:51]=[CH:50][C:46]([C:47]([N:23]3[CH2:24][CH2:25][N:20]([CH2:19][C:17]4[CH:16]=[CH:15][N:14]=[C:13]([C:5]5[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=5)[CH:18]=4)[CH2:21][CH2:22]3)=[O:48])=[CH:45][CH:44]=2)[CH:36]=[C:37]([O:41][CH3:42])[C:38]=1[O:39][CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 120211551-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]-methyl]piperazineHCID 18546780HCID 18546780, compound

Product 1

HCID 18546861HCID 18546861, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl]-piperazine (103 mg) was dissolved in dichloromethane (0.9 mL), and a saturated aqueous solution (0.9 mL) of sodium hydrogencarbonate was added to the solution. 4-(3,4,5-Trimethoxyphenyl)benzoyl chloride (55 mg) was then added dropwise to the mixture under ice cooling, and the resultant mixture was stirred for 1 hour. After water was added to the reaction mixture to conduct extraction with chloroform, the resultant organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=50:1) to obtain the title compound as a free base.

Workup

  1. extractionextraction with chloroform
  2. dry with materialthe resultant organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-a852d5c6df2f4aeea70045290c8d3641
Source dataset
uspto-grants-2003_04
Patent number
US06552188B2

Reaction notes

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