Formaldehyde → HCID 86643939, compound

HRID 2177526Notes

Reaction equation

HRID 2177526 reaction equation
[CH3:1][NH:2][CH:3]([CH3:16])[CH2:4][CH2:5][CH:6]([N+:13]([O-:15])=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:17]=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.C(OCC)(=O)C>[CH3:1][N:2]1[CH2:17][C:6]([N+:13]([O-:15])=[O:14])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH:3]1[CH3:16]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 24436Sodium SulfateHCID 59438390HCID 59438390, compound

Product 1

HCID 86643939HCID 86643939, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 138 mg (0.621 mmol) Methyl-(1-methyl-4-nitro-4-phenyl-butyl)-amine in 2.2 ml dioxane under argon at room temperature, was added 49.8 ul (0.683 mmol) formaldehyde (37% in water). The mixture was stirred at room temperature for 30 minutes and then at 65° C. for 4.5 hours. The mixture was cooled to room temperature and diluted with ethyl acetate. Sodium sulfate was added. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified on silica (Eluent: heptane/ethyl acetate 0 to 20%) to provide 76 mg (52%) of the title compound as a colorless oil. MS (m/e): 235.3 (M+H).

Workup

  1. waitat 65° C. for 4.5 hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified on silica (Eluent: heptane/ethyl acetate 0 to 20%)

Sources & evidence

ORD record
ord-239874a34110414ebb9fbf9e421e70d5
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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