Methyl iodide → HCID 86720919, compound

HRID 524861Notes

Reaction equation

HRID 524861 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]1)([O-])=O.I[CH3:25].[H-].[Na+]>CN(C=O)C.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][CH:13]([N:16]([CH3:25])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86720920HCID 86720920, compound

Product 1

HCID 86720919HCID 86720919, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl N-[1-(3-nitro-4-pyridyl)-4-piperidyl]carbamate (2100 mg, 6.514 mmol) (prepared according to methods similar to the one depicted in Step 1 of Preparation N-1) and iodomethane (4.623 g, 2.028 mL, 32.57 mmol) in DMF at 0° C. was added portionwise sodium hydride (312.7 mg, 7.817 mmol). The reaction was stirred at 0° C. for 1 h, and at room temperature for 1 h. The reaction was quenched by pouring the reaction mixture onto a saturated aqueous solution of ammonium chloride, then extracted with ethyl acetate (2×50 mL). The combined organics was washed with brine (2×50 mL), dried and evaporated to leave an orange solid. To the crude solid dissolved in MeOH (50 mL) was added Pd/C (10%) (346 mg) and the mixture was stirred under a hydrogen atmosphere for 4 h. The reaction was filtered through celite and evaporated to leave tert-butyl (1-(3-aminopyridin-4-yl)piperidin-4-yl)(methyl)carbamate as a yellow oil. (600 mg, 20%) MS (ES+-tBu) 251.1.

Workup

  1. waitat room temperature for 1 h
  2. customThe reaction was quenched
  3. additionby pouring the reaction mixture onto a saturated aqueous solution of ammonium chloride
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe combined organics was washed with brine (2×50 mL)
  6. customdried
  7. customevaporated
  8. customto leave an orange solid
  9. stirringthe mixture was stirred under a hydrogen atmosphere for 4 h
  10. filtrationThe reaction was filtered through celite
  11. customevaporated

Sources & evidence

ORD record
ord-fa675fed32b44e7a8081f9f0a2e0f682
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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