Acetone → HCID 131714202, compound

HRID 462448Notes

Reaction equation

HRID 462448 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][C:22]2[N:23](CC3C=CC=CC=3)[CH:24]=[CH:25][N:26]=2)=[C:9]1[C:34]([O:36][CH2:37][CH3:38])=[O:35].Cl.CC(C)=O>C(O)C.[Pd]>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][C:22]2[NH:26][CH:25]=[CH:24][N:23]=2)=[C:9]1[C:34]([O:36][CH2:37][CH3:38])=[O:35]

Participants

6

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric Acid2×HCID 70466549HCID 70466549, compound

Product 1

HCID 131714202HCID 131714202, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(2-Chlorophenyl)-2-[(1-benzyl-2-imidazolyl)methoxymethyl]-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (Example 10) (2 g) was dissolved in ethanol (70 ml) and acidified with hydrogen chloride gas. Then 10% palladium on charcoal catalyst (0.25 g) was added and the suspension was stirred under hydrogen at 50 p.s.i and room temperature overnight. Examination of the reaction mixture by t.l.c. showed that about one third of the starting material had been converted to a more polar product. The catalyst was removed by filtration, the ethanol was evaporated and the residue partitioned between chloroform (50 ml) and dilute aqueous ammonia (30 ml). The chloroform solution was dried (Na2CO3), filtered and evaporated. The residue was dissolved in a little toluene and chromatographed on silica (t.l.c. grade, 6 g). Elution with toluene removed unreacted starting material; elution with chloroform and then chloroform plus 2-4% v/v methanol gave the product, which was converted to the hydrochloride salt by addition of ethereal hydrogen chloride to an acetone solution of the free base. Recrystallisation of the hydrochloride salt from methanol-ethyl acetate (1:4) gave the title compound (430 mg), m.p. 190° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe ethanol was evaporated
  3. customthe residue partitioned between chloroform (50 ml) and dilute aqueous ammonia (30 ml)
  4. dry with materialThe chloroform solution was dried (Na2CO3)
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue was dissolved in a little toluene
  8. customchromatographed on silica (t.l.c. grade, 6 g)
  9. washElution with toluene removed
  10. washelution with chloroform
  11. customchloroform plus 2-4% v/v methanol gave the product, which
  12. customRecrystallisation of the hydrochloride salt from methanol-ethyl acetate (1:4)

Sources & evidence

ORD record
ord-5bc9a548f9194695859537f6dbd27143
Source dataset
uspto-grants-1985_05
Patent number
US04515799

Reaction notes

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