HCID 59349571, compound → HCID 59349500, compound

HRID 415126Notes

Reaction equation

HRID 415126 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[N+:23]([O-])=O)[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[NH2:23][C:22]1[CH:21]=[CH:20][C:4]([O:5][CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:11][CH2:12]2)=[CH:3][C:2]=1[CH3:1]

Participants

6

Reactant 2

HCID 59349571HCID 59349571, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59349500HCID 59349500, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-((3-methyl-4-nitrophenoxy)methyl)piperidine-1-carboxylate (5.68 g, 16.22 mmoles) was dissolved in ethyl acetate (60 ml) and methanol (40 ml). The solution was treated with 600 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 of hydrogen gas, at room temperature. After 16 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 to give 3.42 g of tert-butyl 4-((4-amino-3-methylphenoxy)methyl)piperidine-1-carboxylate as a pink solid (100% yield). The material was used in the next step without any further purification. 1H-NMR (400 MHz, DMSO-d6) d 6.34 (d, 1H), 6.32 (s, 1H), 6.23 (d, 1H), 5.84 (br s, 2H), 3.90 (s, 2H), 3.34 (m, 4H), 2.00 (m, 1H), 1.46 (m, 4H), 1.42 (s, 9H). MS (EI): 321 (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

Sources & evidence

ORD record
ord-9daa929dd4da4e1d802e08973d906821
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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