Nitrogen → (2-amino-5-ethylphenyl)[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amine

HRID 2064063Notes

Reaction equation

HRID 2064063 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:22]([O-])=O)=[C:7]([NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)[CH:8]=1)=[CH2:2].N#N>CO.[Pd]>[NH2:22][C:6]1[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][C:7]=1[NH:9][CH:10]1[CH2:11][CH2:12][N:13]([CH:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 947NitrogenHCID 59863033N-(5-ethenyl-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine

Product 1

HCID 59863026(2-amino-5-ethylphenyl)[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amineYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of N-(5-ethenyl-2-nitrophenyl)-1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine D25 (416 mg, 1.26 mmol) and NH4HCO2 (792 mg, 12.6 mmol) in methanol (100 mL) was added, under a positive flow of N2, 10% Pd—C (200 mg, 0.189 mmol). The resulted mixture was stirred under room temperature for 1.5 hours and was then filtered through a celite pad. The filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane (100 mL). The resulting solution was washed with saturated NaCl solution (2×100 mL), dried with Na2SO4, and concentrated in vacuo to yield the title compound (251 mg, 66% yield). MS (ESI): 304 [M+H]+.

Workup

  1. filtrationwas then filtered through a celite pad
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  4. washThe resulting solution was washed with saturated NaCl solution (2×100 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-358d6f2b4fc14d6e87058fbdb99ddfd7
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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