N-[(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-cyclohexan-carboxamide → 3,3a,5,6-Tetrahydro-1-cyclohexyl-3a-methyl-4-oxa-2,10b-diazafluoranthene

HRID 647594Notes

Reaction equation

HRID 647594 reaction equation
[CH3:1][C:2]1([CH2:15][NH:16][C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=O)[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3>P(Cl)(Cl)(Cl)=O>[CH:19]1([C:17]2[N:8]3[C:7]4[C:2]([CH3:1])([O:3][CH2:4][CH2:5][C:6]=4[C:14]4[C:9]3=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:15][N:16]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 1

HCID 12708192N-[(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-cyclohexan-carboxamide

Product 1

HCID 566220213,3a,5,6-Tetrahydro-1-cyclohexyl-3a-methyl-4-oxa-2,10b-diazafluorantheneYield 57%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of N-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-cyclohexancarboxamide(1.3 g, described in Example 6) and phosphorus oxychloride (50 ml) is refluxed for 60 minutes and evaporated. The residue is dissolved in chloroform. This solution is washed quickly with 5% sodium hydroxide, dried over magnesium sulfate, filtered and evaporated. The residue is chromatographed on silica gel using chloroform and the eluates are evaporated to give the title compound (0.70 g), nmr(CDCl3) δ0.9-2.6(multiplets), 3.23(d), 3.83(d) and 4.20(m).

Workup

  1. temperatureis refluxed for 60 minutes
  2. customevaporated
  3. dissolutionThe residue is dissolved in chloroform
  4. washThis solution is washed quickly with 5% sodium hydroxide
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is chromatographed on silica gel
  9. customthe eluates are evaporated

Sources & evidence

ORD record
ord-eeac4b1ab19144acb0f5edd361da617a
Source dataset
uspto-grants-1983_10
Patent number
US04409224

Reaction notes

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