HCID 14929460, compound → HCID 43090715, compound

HRID 1429229Notes

Reaction equation

HRID 1429229 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[NH2:8]

Participants

5

Reactant 2

HCID 14929460HCID 14929460, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 43090715HCID 43090715, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-methyl-4-nitrophenyl)piperidine (6.75 g, 30.6 mmol) in ethyl acetate (50 mL) was added 10% palladium on carbon (0.033 g, 0.306 mmol) and the mixture hydrogenated (hydrogen balloon) at room temperature for 20 hours. The mixture was then filtered through diatomaceous earth and washed with ethyl acetate; the filtrate was then concentrated to afford 5.5 g (94%) of the title compound. MS (ESI) m/z 191 (M+H)+.

Workup

  1. filtrationThe mixture was then filtered through diatomaceous earth
  2. washwashed with ethyl acetate
  3. concentrationthe filtrate was then concentrated

Sources & evidence

ORD record
ord-3b4071b3b99b4c18b829a54c430adc02
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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