Methanesulfonic Acid → HCID 10412674, compound

HRID 2107649Notes

Reaction equation

HRID 2107649 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:18]=[CH:19]/[CH:20]=[CH:21]/[C:22]([NH:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH:30]([C:33]3[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[NH:35][CH:34]=3)[CH2:29][CH2:28]2)=[O:23])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[O:9]COCCOC.CS(O)(=O)=O.[OH-].[Na+].C(=O)(O)[O-].[Na+]>CO.O>[OH:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5](/[CH:18]=[CH:19]/[CH:20]=[CH:21]/[C:22]([NH:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH:30]([C:33]3[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[NH:35][CH:34]=3)[CH2:29][CH2:28]2)=[O:23])=[CH:6][C:7]=1[O:16][CH3:17]

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 15257493HCID 15257493, compound

Product 1

HCID 10412674HCID 10412674, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 1-[2-[5-[3,5-dimethoxy-4-{(2-methoxyethoxy)methoxy}phenyl]-(2E,4E)-2,4-pentadienoylamino]ethyl]-4-(3-indolyl)piperidine (10.0 g) in methanol (100 ml) was added slowly methanesulfonic acid (2.3 ml) at ambient temperature. After stirring for 2 hours, the reaction mixture was adjusted to pH 7.2 with aqueous 2N sodium hydroxide solution, and poured into a solution of 4.5 g of sodium bicarbonate in 500 ml of water. After stirring for 30 minutes, the resulting precipitate was collected by filtration and washed with 100 ml of water. The residue was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol. The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from ethanol to give 1-[2-{5-(4-hydroxy-3,5-dimethoxyphenyl)-(2E,4E)-2,4-pentadienoylamino}ethyl]-4-(3-indolyl)piperidine (6.69 g).

Workup

  1. stirringAfter stirring for 30 minutes
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with 100 ml of water
  4. washeluted with a mixture of chloroform and methanol
  5. additionThe fractions containing the object compound
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-40ecf01fd9d04b329191e6a729d3a415
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

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