Potassium Carbonate → HCID 18964000, compound

HRID 2226932Notes

Reaction equation

HRID 2226932 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][C:7]([OH:11])=[CH:6][C:5]=2[C:4]2[CH2:12][CH:13]([CH2:15][NH:16][CH3:17])[CH2:14][C:3]1=2.C([O-])([O-])=O.[K+].[K+].[CH3:24][N:25]=[C:26]=[O:27]>O1CCCC1>[CH3:24][NH:25][C:26](=[O:27])[O:11][C:7]1[CH:8]=[CH:9][C:10]2[N:2]([CH3:1])[C:3]3[CH2:14][CH:13]([CH2:15][NH:16][CH3:17])[CH2:12][C:4]=3[C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 18964019HCID 18964019, compound

Product 1

HCID 18964000HCID 18964000, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2,3,4-tetrahydro-4-methyl-2-[(methylamino)methyl]cyclopent[b]indol-7-ol (1.7 g, 0.007 mole) in 30 ml of tetrahydrofuran, was added milled K2CO3 (1.2 g, 0.01 mole), followed by methyl isocyanate (0.4 ml, 0.07 mole). After stirring at ambient temperature for two hours, the mixture was filtered, and the filtrate concentrated to a yellow oil (~2 g), which was dissolved in ethyl acetate then washed with water and then dried over anhydrous MgSO4. After filtering, the solvent was evaporated to afford a tan solid, ~1.0 g, which was eluted on a silica gel column with 5% methanol/dichloromethane via HPLC. The desired fraction was concentrated to a tan foam (0.8 g, m.p. ~50° C.), which was recrystallized from ethyl ether to give the product as a tan solid, 0.6 g, m.p. 216° C. (dec).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate concentrated to a yellow oil (~2 g), which
  3. dissolutionwas dissolved in ethyl acetate
  4. washthen washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationAfter filtering
  7. customthe solvent was evaporated
  8. customto afford a tan solid, ~1.0 g, which
  9. washwas eluted on a silica gel column with 5% methanol/dichloromethane via HPLC
  10. concentrationThe desired fraction was concentrated to a tan foam (0.8 g, m.p. ~50° C.), which
  11. customwas recrystallized from ethyl ether

Sources & evidence

ORD record
ord-b6fd1e6a10ec4c7bafea215332fff8c2
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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