Acetic Acid → HCID 59427934, compound

HRID 446252Notes

Reaction equation

HRID 446252 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[N+:16]([O-])=O)([CH3:5])[CH2:3]N.C=O.[C:21](O)(=O)C.[C:25]([BH3-])#[N:26].[Na+]>CO.O.ClCCl>[CH3:21][N:26]([CH3:25])[CH2:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[NH2:16])([CH3:5])[CH3:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66970376HCID 66970376, compound

Product 1

HCID 59427934HCID 59427934, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-Methyl-2-(2-nitro-4-trifluoromethyl-phenyl)-propylamine (0.76 g, 2.9 mmol) in methanol (29 mL) at 0 degrees C. was added formaldehyde (0.60 mL of a 37 wt solution in water, excess), acetic acid (0.83 mL, 14.5 mmol), and sodium cyanoborohydride (0.36 g, 5.8 mmol). The homogeneous yellow solution was allowed to warm to room temperature and was stirred overnight. After approximately 12 h, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate until basic. The mixture was concentrated in vacuo, and the resulting material was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed once with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a yellow oil which contained solid material. The oil was dissolved in dichloromethane and filtered through a plug of cotton. Purification by flash chromatography provided the title compound as a yellow oil. MS m/z 291=[M+H]+. Calc'd for C13H17F3N2O2: 290.29.

Workup

  1. customat 0 degrees C
  2. waitAfter approximately 12 h
  3. customthe reaction was quenched by the addition of saturated aqueous sodium bicarbonate until basic
  4. concentrationThe mixture was concentrated in vacuo
  5. customthe resulting material was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  6. washThe organic layer was washed once with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a yellow oil which
  11. filtrationfiltered through a plug of cotton
  12. customPurification by flash chromatography

Sources & evidence

ORD record
ord-e2a29c7da83c42b4ad33430fb61346ee
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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