Water → HCID 86594429, compound

HRID 459856Notes

Reaction equation

HRID 459856 reaction equation
Cl.C([O:4][C:5](=[O:7])[CH3:6])C.[CH3:8][N:9]([CH3:32])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27]C(C)(C)C)=O)[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N([OH:54])N=NC=2C=1.[CH3:55][O:56][C:57]1[CH:58]=[C:59]([C:65]2[N:70]=[C:69]([C:71]([OH:73])=[O:72])[CH:68]=[CH:67][CH:66]=2)[CH:60]=[CH:61][C:62]=1[O:63][CH3:64].[OH2:74]>C(N(CC)CC)C.CN(C=O)C>[C:5]([OH:4])(=[O:7])[C:6]([OH:12])=[O:74].[C:71]([OH:73])(=[O:72])[C:69]([OH:54])=[O:74].[CH3:55][O:56][C:57]1[CH:58]=[C:59]([C:65]2[N:70]=[C:69]([C:25]([N:22]3[CH2:21][CH2:20][N:19]([C:16]4[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][N:9]([CH3:8])[CH3:32])=[CH:18][CH:17]=4)[CH2:24][CH2:23]3)=[O:27])[CH:68]=[CH:67][CH:66]=2)[CH:60]=[CH:61][C:62]=1[O:63][CH3:64]

Participants

9

Reactant 6

HCID 962WaterHCID 757711-Hydroxybenzotriazole2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 21866389Hydrogen chloride-ethyl acetateHCID 220219686-(3,4-Dimethoxyphenyl)pyridine-2-carboxylic acidHCID 22931001HCID 22931001, compound

Product 1

HCID 86594429HCID 86594429, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

In 15 ml of a 4M hydrogen cloride/ethylacetate solution, 0.62 g of t-butyl 4-[4-(2-dimethylaminoethoxy)phenyl]piperazine-1-carboxylate was reacted. To a DMF (15 ml) solution of 0.86 g of a crude product obtained by evaporation of the solvent were added 0.34 g of WSC hydrochloride, 0.24 g of HOBt and 0.41 g of 6-(3,4-dimethoxyphenyl)pyridine-2-carboxylic acid, followed by 65 hours of reaction at room temperature. Further, 0.34 g of WSC hydrochloride, 0.24 g of HOBt and 0.50 ml of triethylamine were added thereto, followed by 8.5 hours of stirring at room temperature. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (ethyl acetate) and then thus obtained compound was subjected to salt formation with 106 mg of oxalic acid. Recrystallization (ethanol) was carried out to obtain 253 mg of 1-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]-4-[4-(2-dimethylaminoethoxy)phenyl]piperazine dioxalate as pale yellow crystals.

Workup

  1. customfollowed by 65 hours of reaction at room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  7. customRecrystallization (ethanol)

Sources & evidence

ORD record
ord-b85b45ac4863471486cd2019ba0d7c8a
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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