Water → HCID 18444269, compound

HRID 459871Notes

Reaction equation

HRID 459871 reaction equation
CN(C=[O:5])C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]2[N:21]=[C:20]([C:22]([N:24]3[CH2:29][CH2:28][N:27]([C:30]4[N:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)=[O:23])[CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].Cl.Cl[CH2:39][CH2:40][N:41]([CH3:43])[CH3:42].[H-].[Na+].[OH2:46]>>[C:13]([OH:14])(=[O:5])[C:8]([OH:7])=[O:46].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]2[N:21]=[C:20]([C:22]([N:24]3[CH2:25][CH2:26][N:27]([C:30]4[CH:31]=[CH:32][C:33]([O:36][CH2:39][CH2:40][N:41]([CH3:43])[CH3:42])=[CH:34][N:35]=4)[CH2:28][CH2:29]3)=[O:23])[CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 18444285HCID 18444285, compound

Product 1

HCID 18444269HCID 18444269, compound

Procedure

To a DMF (5 ml) solution of 213 mg of 6-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}pyridin-3-ol were added 81 mg of (2-chloroethyl)dimethylamine hydrochloride and 43 mg of 60% sodium hydride under ice cooling. After 1 hour of stirring at an oil bath temperature of 70° C., water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate, and thereafter, the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform to chloroform-methanol) and thus obtained product (110 mg) was dissolved in ethanol and converted into its oxalate salt by adding 40 mg of oxalic acid. Thereafter, the salt was recrystallized from ethanol to obtain 81 mg of 1-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-4-[5-(2-dimethylaminoethoxy)-2-pyridyl]piperazine oxalate as colorless crystals.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (chloroform to chloroform-methanol) and thus obtained product (110 mg)
  7. dissolutionwas dissolved in ethanol
  8. additionby adding 40 mg of oxalic acid
  9. customThereafter, the salt was recrystallized from ethanol

Sources & evidence

ORD record
ord-9f322e4372b24324bd21e4889a08fd09
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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