HCID 19915408, compound → HCID 19915418, compound

HRID 1090478Notes

Reaction equation

HRID 1090478 reaction equation
[ClH:1].[CH3:2][NH:3][C:4]12[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH:9]1[CH2:8][CH:7]=[CH:6][CH2:5]2.[H][H]>CO.[Pd]>[ClH:1].[CH3:2][NH:3][C:4]12[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 19915408HCID 19915408, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19915418HCID 19915418, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

General procedure: A solution of 5 g of N-methyl- 1,4,9,9a-tetrahydro-4aH-fluoren-4a-amine hydrochloride in 100 ml of methanol is hydrogenated by shaking it with 0.5 g of 20% palladium on charcoal catalyst in contact with a hydrogen atmosphere. When the theoretical amount of hydrogen corresponding to hydrogenation of one double bond has been absorbed, the catalyst is removed by filtration and the solvent distilled under reduced pressure to yield N-methyl-1,2,3,4,9,9a-hexahydro-4aH-fluoren-4a-amine hydrochloride; mp 202° C. to 203° C. following recrystallization from methanol-ether. The free base is obtained by treating an aqueous solution of the hydrochloride with sodium hydroxide and extracting with ether. The hydrobromide is obtained by adding a slight excess of hydrogen bromide to a solution of the free base in ether.

Workup

  1. customWhen the theoretical amount of hydrogen corresponding to hydrogenation of one double bond has been absorbed
  2. customthe catalyst is removed by filtration
  3. distillationthe solvent distilled under reduced pressure

Sources & evidence

ORD record
ord-c82396ac0d49458592997e9984adabbe
Source dataset
uspto-grants-1992_01
Patent number
US05081304

Reaction notes

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