Formaldehyde → HCID 59353077, compound

HRID 1914684Notes

Reaction equation

HRID 1914684 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH:7]=[C:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[NH:11][C:10]([CH3:17])([CH3:16])[CH2:9]2)=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1.C=O.[C:25]([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH:7]=[C:8]2[CH2:9][C:10]([CH3:17])([CH3:16])[N:11]([CH3:25])[C:12]([CH3:14])([CH3:15])[CH2:13]2)=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 59353082HCID 59353082, compound

Product 1

HCID 59353077HCID 59353077, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(4-methoxy-2-nitrobenzylidene)-2,2,6,6-tetramethylpiperidine (1.1 g; 3.23 mmol; 1 eq) is dissolved in MeOH (10 mL) then formaldehyde (0.19 g; 6.45 mmol; 2 eq) and sodium cyanoborohydride (0.41 g; 6.45 mmol; 2 eq) are added. The reaction mixture is stirred at room temperature overnight. The solvents are evaporated under reduced pressure and the residue obtained is taken up in EtOAc then a saturated aqueous solution of NaHCO3 is added. The organic phase is washed with brine, dried over MgSO4 and the solvent is evaporated under reduced pressure to afford 320 mg (31%) of the title compound as a yellow oil. 1H NMR (DMSO-d6) δ 7.53 (d, J=2.6 Hz, 1H), 7.20 (d, J=8.2 Hz, 1H), 7.10 (dd, J=8.6, 2.6 Hz, 1H), 6.49 (s, 1H), 3.87 (s, 3H), 2.22-2.15 (m, 6H), 1.20-1.10 (m, 6H), 1.00-0.90 (m, 6H). HPLC (max plot) 99.5%; Rt 2.84 min. LC/MS: (ES+): 319.1

Workup

  1. customThe solvents are evaporated under reduced pressure
  2. customthe residue obtained
  3. washThe organic phase is washed with brine
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-2c724443dc35487186dd48135da9e0aa
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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