HCID 131718665, compound → HCID 131718664, compound

HRID 2226114Notes

Reaction equation

HRID 2226114 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]2[C@@H:16]([NH:17][C:18](=O)[C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([NH:26][S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[CH:20]=3)[CH2:15][CH2:14][N:13]([CH3:38])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>O=P(Cl)(Cl)Cl>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[C@H:11]3[C@H:16]([CH2:15][CH2:14][N:13]([CH3:38])[CH2:12]3)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([NH:26][S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[CH:20]=3)[C:6]=2[CH:7]=1

Participants

3

Reactant 1

HCID 131718665HCID 131718665, compound

Product 1

HCID 131718664HCID 131718664, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

3.9 g rac-cis-3-(3,4-dimethoxyphenyl)-1-methyl-4-[4-methyl-3-(p-toluene-sulphonamido)-benzamido]-piperidine are heated at the boiling point under reflux in 50 ml phosphorus oxytrichloride for 3 h. After the excess phosphorus oxytrichloride has been distilled off, the residue is partitioned between methylene chloride and 2 N sodium hydroxide solution, and the organic phase is washed with water and dried over sodium sulphate. After the methylene chloride has been distilled off, the residue is purified by silica gel chromatography. The main product fraction which has been separated off is concentrated and the solid residue is recrystallized from ethyl acetate/petroleum ether. 2.6 g of the title compound are obtained as yellowish crystals of m.p. 206°-210° C. (decomp.).

Workup

  1. distillationAfter the excess phosphorus oxytrichloride has been distilled off
  2. customthe residue is partitioned between methylene chloride and 2 N sodium hydroxide solution
  3. washthe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. distillationAfter the methylene chloride has been distilled off
  6. customthe residue is purified by silica gel chromatography
  7. customThe main product fraction which has been separated off
  8. concentrationis concentrated
  9. customthe solid residue is recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-73623b59b6f44991a38689bd414e3556
Source dataset
uspto-grants-1994_09
Patent number
US05346904

Reaction notes

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