Sodium Carbonate → HCID 23046187, compound

HRID 2107650Notes

Reaction equation

HRID 2107650 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][CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([C:34]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[NH:36][CH:35]=3)[CH2:30][CH2:29]2)=[O:23])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[O:9]COCCOC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[OH:9][C:8]1[C:7]([O:16][CH3:17])=[CH:6][C:5](/[CH:18]=[CH:19]/[CH:20]=[CH:21]/[C:22]([NH:24][CH2:25][CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH:31]([C:34]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[NH:36][CH:35]=3)[CH2:32][CH2:33]2)=[O:23])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23046192HCID 23046192, compound

Product 1

HCID 23046187HCID 23046187, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[3-[5-[3,5-dimethoxy-4-{(2-methoxyethoxy)methoxy}phenyl]-(2E,4E)-2,4-pentadienoylamino]propyl]-4-(3-indolyl)piperidine (1.67 g) and p-toluenesulfonic acid monohydrate (0.64 g) in methanol (33 ml) was refluxed for 30 minutes under an inert atmosphere. Upon cooling to ambient temperature, the mixture was added dropwise to an aqueous sodium carbonate solution. The resulting powder was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol (10:1 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure. The obtained residue was recrystallized from a mixture of ethanol and water (7:3 V/V) to give 1-[3-{5-(4-hydroxy-3,5-dimethoxyphenyl)-(2E,4E)-2,4-pentadienoylamino}propyl]-4-(3-indolyl)piperidine (0.51 g).

Workup

  1. temperaturewas refluxed for 30 minutes under an inert atmosphere
  2. washeluted with a mixture of chloroform and methanol (10:1 V/V)
  3. additionThe fractions containing the object compound
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was recrystallized from a mixture of ethanol and water (7:3 V/V)

Sources & evidence

ORD record
ord-a268b6218dd4477992d01215d1866e8e
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

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