Isopropylamine → Indecainide

HRID 1153873Notes

Reaction equation

HRID 1153873 reaction equation
O[CH:2]1[NH:7][C:6](=[O:8])[C:5]2([C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:4][CH2:3]1.[H][H].[CH:23]([NH2:26])([CH3:25])[CH3:24]>[Pd]>[C:6]([C:5]1([CH2:4][CH2:3][CH2:2][NH:26][CH:23]([CH3:25])[CH3:24])[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)(=[O:8])[NH2:7]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 133680416'-hydroxyspiro(9H-fluorene-9,3'-piperidine)-2'-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 52195Indecainide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The general procedure described above was followed when 6'-Hydroxyspiro-(9H-fluorene-9,3'-piperidine)-2'-one (2.7 g) was dissolved in isopropylamine (350 ml) and 10% palladium on charcoal (0.3 g) was added and the vessel pressurized to 90 p.s.i. with hydrogen. The reaction mixture was then heated at 40° for 16 hours and then allowed to cool to room temperature. The catalyst was removed by filtration and the isopropylamine evaporated under reduced pressure. The resulting residue was dissolved in dichloromethane (20 ml) washed with water (2×50 ml), dried with anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue was triturated with hexane to give 9-carbamoyl-9-(3-isopropylaminopropyl)fluorene crystals.

Workup

  1. temperatureThe reaction mixture was then heated at 40° for 16 hours
  2. customThe catalyst was removed by filtration
  3. customthe isopropylamine evaporated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in dichloromethane (20 ml)
  5. washwashed with water (2×50 ml)
  6. dry with materialdried with anhydrous sodium sulphate
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-47769892be5f43c789762af7af4517e3
Source dataset
uspto-grants-1984_12
Patent number
US04486592

Reaction notes

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