p-Toluenesulfonic acid monohydrate → HCID 15257490, compound

HRID 2107651Notes

Reaction equation

HRID 2107651 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 refluxed 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. temperaturewas refluxed for 30 minutes under an inert atmosphere
  2. customAfter the solvent was removed under reduced pressure
  3. additionthe residue was treated with water (100 ml)
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customAfter removal of the solvent
  8. washeluted with a mixture of chloroform and methanol (8:1 V/V)
  9. additionThe fractions containing the object compound
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5482ae9394984a94be6c1d422fe00cf8
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

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