Ethanol → HCID 14031281, compound

HRID 247387Notes

Reaction equation

HRID 247387 reaction equation
[CH2:1]1[C:12]2[CH:4]([NH:5][CH:6]3[C:11]=2[C:10](=[O:13])[CH:9]=[CH:8][CH2:7]3)[CH2:3][CH2:2]1.Cl.[CH3:15][NH:16][CH3:17].C=O.[CH2:20](O)C>C(O)(=O)C.O.CO.C(Cl)(Cl)Cl>[CH3:15][N:16]([CH2:20][CH:9]1[CH2:8][CH2:7][C:6]2[NH:5][C:4]3[CH2:3][CH2:2][CH2:1][C:12]=3[C:11]=2[C:10]1=[O:13])[CH3:17]

Participants

9

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 70421324HCID 70421324, compound

Product 1

HCID 14031281HCID 14031281, compoundYield 36%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 14.0 g (0.08 mole) of cyclopent[b]indolone of Example 8, 9.96 g (0.12 mole) of dimethylamine hydrochloride and 7.2 g (0.24 mole) of paraformaldehyde in 280 mL of 2B ethanol was heated to reflux and stirred mechanically for 20 hours. The solvent was removed on a rotary evaporator at 35° C. The residue showed unreacted cyclopent[b]indolone of Example 8, the desired title compound and a third component, identified as an ethoxymethyl substituted compound by thin layer chromatography. The residue was chromatographed on silica gel (dry column) eluting with the lower phase of a mixture prepared by shaking 90 parts CHCl3, 30 parts CH3OH, 10 parts H2O, and 6 parts acetic acid. Fractions containing starting the ketone and the ethoxymethyl substituted compound eluted first. The fractions containing the title compound were washed with 10% NH4OH, dried over Na2SO4, and concentrated on a rotary evaporator to give 6.7 g (36%) of title compound as an off-white solid. A sample, recrystallized from ethanol, had mp 165°-166° C.

Workup

  1. temperatureto reflux
  2. customThe solvent was removed on a rotary evaporator at 35° C
  3. customThe residue was chromatographed on silica gel (dry column)
  4. washeluting with the lower phase of a mixture
  5. customprepared
  6. additionFractions containing
  7. washthe ethoxymethyl substituted compound eluted first
  8. additionThe fractions containing the title compound
  9. washwere washed with 10% NH4OH
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-b97786e1564749b5b05af0fc0cf1063d
Source dataset
uspto-grants-1987_11
Patent number
US04707484

Reaction notes

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