Isopropylamine → Indecainide

HRID 1381330Notes

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

Conditions

Temperature: 40 °C

Procedure

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 pressurised to 90 p.s.i. with hydrogen. The reaction mixture was then heated at 40° C. 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 the title compound as white crystals, the identity of which was confirmed by thin layer chromatographic comparison with an authentic sample (silica gel, ethylacetate:methanol 80:20 v/v).

Workup

temperatureto cool to room temperature
customThe catalyst was removed by filtration
customthe isopropylamine evaporated under reduced pressure
dissolutionThe resulting residue was dissolved in dichloromethane (20 ml)
washwashed with water (2×50 ml)
dry with materialdried with anhydrous sodium sulphate
customevaporated to dryness under reduced pressure
customThe residue was triturated with hexane

Sources & evidence

ORD record: ord-46165600231a41eb961420b8ed8e4c0a
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04585894

Reaction notes

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