9-(2-Cyanoethyl)-9H-fluorene-9-carboxamide → Deisopropylindecainide

HRID 1277475Notes

Reaction equation

HRID 1277475 reaction equation
[NH2:1][C:2]([C:4]1([CH2:17][CH2:18][C:19]#[N:20])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:3].[H][H]>[Pt]=O.C(O)(=O)C>[NH2:20][CH2:19][CH2:18][CH2:17][C:4]1([C:2]([NH2:1])=[O:3])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

5

Reactant 2

HCID 30188199-(2-Cyanoethyl)-9H-fluorene-9-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 127612Deisopropylindecainide

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A 3.3 g. portion of 9-aminocarbonyl-9-(2-cyanoethyl)fluorene from Example 27 was hydrogenated in 95 ml. of glacial acetic acid under 4 atmospheres of hydrogen pressure for two hours at 24° C. in the presence of 1.5g. of platinum oxide catalyst. The reaction mixture was filtered to remove the catalyst and the solvent was removed by evaporation under reduced pressure. The product which remained was dissolved in ethyl acetate and then extracted into 1 N hydrochloric acid. The aqueous acid layer was separated, made alkaline with 50% sodium hydroxide, and extracted several times with fresh ethyl acetate. The extracts were combined, washed with water and with brine, dried, and the solvent was removed by evaporation under reduced pressure to provide 2.3 g of a white solid. The solid was dissolved in 1 N hydrochloric acid, filtered, and diluted with water to 100 ml. The aqueous acid solution was lyophilized to provide a white solid, which when crystallized from methanol and ethyl acetate was identified as 1.0 g. of 9-(3-aminopropyl)-9-aminocarbonylfluorene. m.p. 198°-200° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. customthe solvent was removed by evaporation under reduced pressure
  4. dissolutionThe product which remained was dissolved in ethyl acetate
  5. extractionextracted into 1 N hydrochloric acid
  6. customThe aqueous acid layer was separated
  7. extractionextracted several times with fresh ethyl acetate
  8. washwashed with water and with brine
  9. customdried
  10. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7b9f917c8be5410ebe8ae7c16d3291fc
Source dataset
uspto-grants-1981_07
Patent number
US04277495

Reaction notes

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