Acetic Acid → Deisopropylindecainide

HRID 1262508Notes

Reaction equation

HRID 1262508 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].C(O)(=O)C.[H][H]>[Pt]=O.Cl>[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

6

Reactant 3

HCID 176Acetic AcidHCID 30188199-(2-Cyanoethyl)-9H-fluorene-9-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 127612Deisopropylindecainide

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 313Hydrochloric 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 1.5 g. 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 1N 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 1N 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 1N 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
  11. customto provide 2.3 g
  12. filtrationfiltered
  13. additiondiluted with water to 100 ml
  14. customto provide a white solid, which when
  15. customcrystallized from methanol and ethyl acetate

Sources & evidence

ORD record
ord-bb484ec98a4243c1bb48461ce76ec175
Source dataset
uspto-grants-1984_06
Patent number
US04452745

Reaction notes

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