p-Toluenesulfonic acid monohydrate → HCID 15257490, compound

HRID 2051397Notes

Reaction equation

HRID 2051397 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:16]=[CH:17]/[C:18]([NH:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([C:29]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[NH:31][CH:30]=3)[CH2:25][CH2:24]2)=[O:19])[CH:6]=[CH:7][C:8]=1[O:9]COCCOC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:9][C:8]1[CH:7]=[CH:6][C:5](/[CH:16]=[CH:17]/[C:18]([NH:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([C:29]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[NH:31][CH:30]=3)[CH2:27][CH2:28]2)=[O:19])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 15257507HCID 15257507, compound

Product 1

HCID 15257490HCID 15257490, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[2-[3-[3-methoxy-4-{(2-methoxyethoxy)-methoxy}phenyl]-(E)-propenoylamino]ethyl]-4-(3-indolyl)-piperidine (2 g) and p-toluenesulfonic acid monohydrate (1.05 g) in methanol (40 ml) was efluxed for 30 minutes under an inert atmosphere. After the solvent was removed under reduced pressure, the residue was treated with water (100 ml), adjusted to pH 10.0 with a sodium carbonate solution and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution and dried over magnesium sulfate. After removal of the solvent, the residue was subjected to column chromatography on silica gel (31 g) and eluted with a mixture of chloroform and methanol (8:1 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure to give 1-[2-{3-(4-hydroxy-3-methoxyphenyl)-(E)-propenoylamino}ethyl]-4-(3-indolyl)piperidine (0.89 g).

Workup

  1. customAfter the solvent was removed under reduced pressure
  2. additionthe residue was treated with water (100 ml)
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of the solvent
  7. washeluted with a mixture of chloroform and methanol (8:1 V/V)
  8. additionThe fractions containing the object compound
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac01b98cd7e640298ea1e9114bf5fbb7
Source dataset
uspto-grants-1991_05
Patent number
US05017703

Reaction notes

Loading…