Pyridine → HCID 19432871, compound

HRID 1736379Notes

Reaction equation

HRID 1736379 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[NH2:15][CH2:16][C:17]([CH:19]1[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1)=[O:18].[C:27](Cl)(=[O:29])[CH3:28].N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:27]([NH:15][CH2:16][C:17]([CH:19]1[CH:24]2[CH2:23][CH2:22][N:21]([CH2:26][CH2:25]2)[CH2:20]1)=[O:18])(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 19432875HCID 19432875, compound

Product 1

HCID 19432871HCID 19432871, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of the dihydrochloride salt of (±) 3-(α-aminoacetyl)-1-azabicyclo[2.2.2]octane (D14) (0.8 g; 0.0033 mole) in absolute chloroform (30 ml) was treated with acetyl chloride (0.76 g, 0.01 mole) and pyridine (4.58 g, 0.058 mole) at 0° C. for 1/2 h. The reaction was allowed to warm to room temperature for 15 h and then concentrated in vacuo. The residue was partitioned between chloroform and saturated aqueous potassium carbonate solution. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo to a gum, which was chromatographed on neutral alumina in 10% methanol in ethyl acetate. This afforded the title compound as an oil (0.4 g, 58%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between chloroform and saturated aqueous potassium carbonate solution
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo to a gum, which
  6. customwas chromatographed on neutral alumina in 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-51ba0d3a6008414ea048b36d103e41f2
Source dataset
uspto-grants-1996_07
Patent number
US05541194

Reaction notes

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