Acetic acid ethanol → HCID 21405550, compound

HRID 972828Notes

Reaction equation

HRID 972828 reaction equation
[ClH:1].[CH2:2]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[C:14](=[O:15])[C:13]3=[CH:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=[C:12]3[C:11]2=[O:23])[CH2:6][CH2:5]1)[CH3:3].[H][H].C(O)(=O)C.C(O)C>C(O)(=O)C.[Pd]>[OH2:15].[ClH:1].[NH2:20][C:17]1[CH:16]=[C:13]2[C:14](=[O:15])[N:10]([CH:7]3[CH2:8][CH2:9][N:4]([CH2:2][CH3:3])[CH2:5][CH2:6]3)[C:11](=[O:23])[C:12]2=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 18476134Acetic acid ethanolHCID 21405573HCID 21405573, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21405550HCID 21405550, compoundYield 144%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1.7 grams (0.005 mole) of 1-ethyl-4-(4-nitrophthalimido)piperidine hydrochloride in 60 milliliters of glacial acetic acid was hydrogenated over 0.1 grams of 10% palladium on carbon catalyst at 50 p.s.i. After the theoretical uptake of hydrogen, a little acetic acid/ethanol mixture was added to dissolve precipitated solid; the catalyst was filtered off, the solvents evaporated and the residue trituated with ether to give a yellow solid. Recrystallisation from methanol gave 1.18 grams of 4-(4-aminophthalimido)-1-ethylpiperidine hydrochloride hydrate, m.p. 254° C(decomp).

Workup

  1. dissolutionto dissolve
  2. customprecipitated solid
  3. filtrationthe catalyst was filtered off
  4. customthe solvents evaporated
  5. customthe residue trituated with ether to give a yellow solid
  6. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-3982ab3f9e704e97b503abe9394189f6
Source dataset
uspto-grants-1977_10
Patent number
US04053615

Reaction notes

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