Water → HCID 10132932, compound

HRID 1386509Notes

Reaction equation

HRID 1386509 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([CH:16]([CH3:18])[CH3:17])([CH2:12][CH2:13][CH2:14]Cl)[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:19](CN)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O.[CH3:35][N:36](C)C=O>>[F:1][C:2]1[CH:3]=[C:4]([C:9]([CH:16]([CH3:18])[CH3:17])([CH2:12][CH2:13][CH2:14][N:36]([CH3:35])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 5

HCID 962Water2×HCID 1001PhenethylamineHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 15281642HCID 15281642, compound

Product 1

HCID 10132932HCID 10132932, compound

Procedure

The product of Example 1, Step (b), (0.54 g, 0.0020 mole), N-benzylmethylamine (0.29 g, 0.0024 mole) and potassium carbonate (0.33 g, 0.0024 mole) were stirred in dimethylformamide (25 mL) for 10 days at room temperature. The mixture was concentrated in vacuo. Water (25 mL) and ethyl acetate (25 mL) were added to the residue. The layers were separated and the aqueous layer was washed with ethyl acetate (25 mL). The ethyl acetate layer and washes were combined and dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The product was purified by silica gel chromatography to give an oil. The structure was supported by NMR, infrared spectroscopy and elemental analysis (M.W.=356.46+0.15 mole H2O). Analysis: Calcd. for C22H26N2F2•0.15 M H2O): C, 73.57; H, 7.38; N, 7.80; Found: C, 73.57; H, 7.33; N, 7.71.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionWater (25 mL) and ethyl acetate (25 mL) were added to the residue
  3. customThe layers were separated
  4. washthe aqueous layer was washed with ethyl acetate (25 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by silica gel chromatography
  9. customto give an oil

Sources & evidence

ORD record
ord-4a2ddb49bb4c4248a5b8460deacb6f0b
Source dataset
uspto-grants-2001_07
Patent number
US06265439B1

Reaction notes

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