1-Methyl-4-(methylamino)piperidine → Methyl-(1-methyl-piperidin-4-yl)-(5-nitro-benzooxazol-2-yl)-amine

HRID 601547Notes

Reaction equation

HRID 601547 reaction equation
C(S[C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:7]=2[N:8]=1)C.[CH3:16][NH:17][CH:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1>C1COCC1>[CH3:16][N:17]([CH:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1)[C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 5663231-Methyl-4-(methylamino)piperidineHCID 574214952-Ethylsulfanyl-5-nitrobenzooxazole

Product 1

HCID 59558006Methyl-(1-methyl-piperidin-4-yl)-(5-nitro-benzooxazol-2-yl)-amineYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve 2-ethylsulfanyl-5-nitro-benzooxazole (1.17 g, 5.23 mmol) in anhydrous THF (10 mL) in a reaction tube and blow nitrogen into the vessel for 10 s. Add methyl-(1-methyl-piperidin-4-yl)-amine (1.37 mL, 9.42 mmol) to the solution. Quickly seal the vessel and immerse into a pre-heated oil bath (100° C.) and stir for 24 h. Concentrate the reaction mixture in vacuo, wash with 1.0M NaOH (aq) (2×50 mL), dry over Na2SO4, filter, and concentrate in vacuo. Subject the residue by silica gel flash column chromatography, eluting with 2N NH3 in MeOH/CH2Cl2, to yield the desired product (0.608 g, 40%). MS (ES+) 291.0 (M+1)+.

Workup

  1. customfor 10 s
  2. customQuickly seal the vessel
  3. customimmerse into a pre-heated oil bath
  4. concentrationConcentrate the reaction mixture in vacuo
  5. washwash with 1.0M NaOH (aq) (2×50 mL)
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. washeluting with 2N NH3 in MeOH/CH2Cl2

Sources & evidence

ORD record
ord-bd698e6a1a864586b461f519f8a0c9ae
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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