Acetic Acid → HCID 66970338, compound

HRID 1361598Notes

Reaction equation

HRID 1361598 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-:18])=[O:17])([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]([CH3:5])([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-:18])=[O:17])[CH3:3]

Participants

8

Reactant 4

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

Product 1

HCID 66970338HCID 66970338, 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.

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-16ec7101684d4d74804e7d63ec91c00c
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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