Hydrochloric Acid → Tert-butyl 4-((4-aminophenoxy)methyl)piperidine-1-carboxylate

HRID 1079388Notes

Reaction equation

HRID 1079388 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23366891Tert-butyl 4-((4-nitrophenyloxy)methyl)piperidine-1-carboxylate

Product 1

HCID 23366952Tert-butyl 4-((4-aminophenoxy)methyl)piperidine-1-carboxylateYield 57.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-tert-Butyloxycarbonyl-4-[(4-nitrophenyloxy)methyl]piperidine (1.9 g) was dissolved in ethanol (40 ml) and to the mixture was added conc. hydrochloric acid (0.5 ml). By using 10% palladium/carbon as a catalyst, catalytic reduction was conducted at normal pressure and room temperature overnight. After completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The concentrate was diluted with methylene chloride and washed with aqueous saturated solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1 (v/v)) to obtain 1-tert-butyloxycarbonyl-4-[(4-aminophenyloxy)methyl]piperidine (1.0 g) as white crystals, m.p. 100°-101° C.

Workup

  1. customwas conducted at normal pressure and room temperature overnight
  2. customAfter completion of the reaction
  3. customthe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionThe concentrate was diluted with methylene chloride
  6. washwashed with aqueous saturated solution of sodium bicarbonate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1 (v/v))

Sources & evidence

ORD record
ord-73b3a9cf9ddd4ea4b09456a557ad4914
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

Loading…