Water → HCID 19754261, compound

HRID 1588746Notes

Reaction equation

HRID 1588746 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]2[N:12]([CH:13]=1)[CH:11]=[CH:10][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8]2)[CH2:2][CH2:3][CH3:4].[CH2:19]([N:23]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)[CH2:20][CH2:21][CH3:22].O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:1]([C:5]1[CH:6]=[C:7]2[N:12]([C:13]=1[C:32](=[O:33])[C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][CH2:24][N:23]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:37][CH2:38][CH2:39][CH3:40])=[CH:36][CH:35]=1)[CH:11]=[CH:10][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 10109258Benzoyl chloride, 4-[3-(dibutylaMino)propoxy]-HCID 18519430HCID 18519430, compound

Product 1

HCID 19754261HCID 19754261, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.35 g (38 mmoles) of 2-n-butyl 7-carbethoxy indolizine and 14.2 g (38 mmoles) of 4-(3-di-n-butylamino-propoxy) benzoyl chloride is heated at 95°-100° C. for 4.5 h. The crude product obtained is dissolved in ethyl acetate and water and is neutralized by sodium hydrogen carbonate. The organic layer is separated and dried over magnesium sulfate. It is filtered and the solvent evaporated. The residue is then purified on a column of silica with ethyl acetate as eluant in order to obtain 7.6 g of the desired compound in the form of the free base (yield: 97%). The oxalic acid salt is then formed in ethyl acetate and recovered by filtration.

Workup

  1. temperatureis heated at 95°-100° C. for 4.5 h
  2. customThe crude product obtained
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationIt is filtered
  6. customthe solvent evaporated
  7. customThe residue is then purified on a column of silica with ethyl acetate as eluant in order

Sources & evidence

ORD record
ord-fdd188d7835f400c8d0fd1a9e1fce75c
Source dataset
uspto-grants-1993_06
Patent number
US05223510

Reaction notes

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