Tert-butyl 4-(3-methyl-4-nitrophenoxy)piperidine-1-carboxylate → Tert-butyl 4-(3-methyl-4-aminophenoxy)piperidine-1-carboxylate

HRID 415068Notes

Reaction equation

HRID 415068 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N+:22]([O-])=O)[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[NH2:22])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:8][CH2:7]1

Participants

6

Reactant 2

HCID 18542679Tert-butyl 4-(3-methyl-4-nitrophenoxy)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18542772Tert-butyl 4-(3-methyl-4-aminophenoxy)piperidine-1-carboxylateYield 111.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(3-methyl-4-nitrophenoxy)piperidine-1-carboxylate (5.2 g, 14.30 mmoles) was dissolved in ethyl acetate (60 ml) and methanol (10 ml). The solution was treated with 500 mg of 10% palladium on carbon (50% water w/w). The slurry was then shaken on a Parr hydrogenator and treated with a 40 psi atmosphere of hydrogen gas, at room temperature. After 18 hours, the slurry was filtered through a plug of Celite, which was subsequently washed with ethyl acetate (50 ml) and methanol (50 ml). The resulting filtrate was then evaporated at reduced pressure and then triturated with hexane to give a solid. This material was filtered off and dried at reduced pressure to give 4.87 g of tert-butyl 4-(3-methyl-4-aminophenoxy)piperidine-1-carboxylate (100% yield). 1H-NMR (400 MHz, DMSO-d6) δ 6.33 (d, 1H), 6.32 (s, 1H), 6.23 (s, 1H), 5.85 (bs, 2H), 3.70 (m, 1H), 3.39 (m, 2H), 3.29 (m, 2H), 2.35 (s, 3H), 2.00 (m, 2H), 1.75 (m, 2H), 1.42 (s, 9H). MS (EI): for C18H28N2O3: 320 (MH+).

Workup

  1. filtrationthe slurry was filtered through a plug of Celite, which
  2. washwas subsequently washed with ethyl acetate (50 ml) and methanol (50 ml)
  3. customThe resulting filtrate was then evaporated at reduced pressure
  4. customtriturated with hexane
  5. customto give a solid
  6. filtrationThis material was filtered off
  7. customdried at reduced pressure

Sources & evidence

ORD record
ord-dcf5532ccad145d7a9c2bdc024e0cd32
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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