Hydrochloric Acid → 1-Tert-butyloxycarbonyl-4-(4-amino-3-methylphenyloxy)piperidine hydrochloride

HRID 1079404Notes

Reaction equation

HRID 1079404 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([CH3:24])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[ClH:25]>C(O)C.[Pd]>[ClH:25].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([CH3:24])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18542679Tert-butyl 4-(3-methyl-4-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 233668921-Tert-butyloxycarbonyl-4-(4-amino-3-methylphenyloxy)piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-tert-butyloxycarbonyl-4-(4-nitro-3-methylphenyloxy)piperidine (3.6 g) in ethanol (30 ml) was added conc. hydrochloric acid (0.9 ml). By using 10% palladium/carbon (containing 48% water, 0.3 g) as a catalyst, catalytic reduction was conducted under reduced pressure for 1.5 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to obtain 1-tert-butyloxycarbonyl-4-(4-amino-3methylphenyloxy)piperidine hydrochloride (1.7 g) as light brown crystals, m.p. 160°-180° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e84e5074125b47359766b579fcc246ce
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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