Sodium Hydroxide → HCID 18962967, compound

HRID 1707272Notes

Reaction equation

HRID 1707272 reaction equation
Cl.[C:2]([C:5]1[CH:6]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([N+:43]([O-:45])=[O:44])[CH:38]=2)[C:7]([C:13](=[O:36])[CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])(=[O:4])[CH3:3].[OH-].[Na+].[C:48]([OH:55])(=[O:54])/[CH:49]=[CH:50]/[C:51]([OH:53])=[O:52]>C(O)(C)C.[O-2].[O-2].[Mn+4]>[C:48]([OH:55])(=[O:54])/[CH:49]=[CH:50]/[C:51]([OH:53])=[O:52].[C:2]([C:5]1[C:6]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([N+:43]([O-:45])=[O:44])[CH:38]=2)=[C:7]([C:13](=[O:36])[CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[C:8]([CH3:12])=[N:9][C:10]=1[CH3:11])(=[O:4])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 18962987HCID 18962987, compound

Product 1

HCID 18962967HCID 18962967, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 3776IsopropanolSolvent2×

Procedure

1.2 g (1.9 mmol) 5-acetyl-1,4-dihydro-2,6-dimethyl-3-[5-(4,4-diphenyl-1-piperidinyl)pentanoyl)-4-(3-nitrophenyl)-pyridine hydrochloride are converted into the free base by shaking with excess 1N NaOH, and the base is extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and concentrated. The residue is dried in vacuo and is then taken up in 30 ml anhydrous methylene chloride. 2.5 g(29 mmol) manganese dioxide are added. The mixture is stirred vigorously at room temperature for 12 h. Another 2 g (23 mmol) manganese dioxide are added in portions of 0.5 g each in the course of a further 8 h. The mixture is then centrifuged and the sediment is decanted off. The supernatant is concentrated and the residue is chromatographed over silica gel with toluene/acetone=8/2. The product thus obtained is taken up in 30 ml isopropanol, and 0.22 g (1.9 mmol) fumaric acid in 20 ml isopropanol is added. The title compound crystallized overnight. Yield: 0.7 g (52%). M.p.: 181°-190° C. decomp. (acetonitrile).

Workup

  1. extractionthe base is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is dried in vacuo
  6. customthe sediment is decanted off
  7. concentrationThe supernatant is concentrated
  8. customthe residue is chromatographed over silica gel with toluene/acetone=8/2
  9. customThe product thus obtained
  10. customThe title compound crystallized overnight

Sources & evidence

ORD record
ord-7e42369fd5024143830bc4f3c75f2b66
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

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