Pyridine → HCID 14654935, compound

HRID 892979Notes

Reaction equation

HRID 892979 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17]C=1>>[N:15]1([C:4]2[N:3]=[C:2]([N:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)[CH:7]=[CH:6][CH:5]=2)[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 4837PiperazineHCID 169892,6-Dichloropyridine

Product 1

HCID 14654935HCID 14654935, compound

Procedure

A solution of 2,6-dichloropyridine (10 g) and piperazine (25 g) in pyridine (30 ml) is stirred at 65° for 3 h and at 20°-25° overnight. The reaction mixture is concentrated, the residue is partitioned between ether and aqueous potassium carbonate. The organic phase is separated, washed with saline, dried over sodium sulfate and concentrated. The residue is added to pyrrolidine (15 g), pyridine (100 ml) and heated at 100° for 6 days. The reaction mixture is concentrated. The residue is partitioned between methylene chloride and aqueous sodium bicarbonate. The organic phase is separated, dried and concentrated. The residue is chromatographed on silica gel, eluting with methanol/ammonium hydroxide/methylene chloride (15/1/84). The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 1.9, 2.9, 3.4, 5.75, 6.5, 7.3 δ.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is partitioned between ether and aqueous potassium carbonate
  3. customThe organic phase is separated
  4. washwashed with saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. additionThe residue is added to pyrrolidine (15 g), pyridine (100 ml)
  8. temperatureheated at 100° for 6 days
  9. concentrationThe reaction mixture is concentrated
  10. customThe residue is partitioned between methylene chloride and aqueous sodium bicarbonate
  11. customThe organic phase is separated
  12. customdried
  13. concentrationconcentrated
  14. customThe residue is chromatographed on silica gel
  15. washeluting with methanol/ammonium hydroxide/methylene chloride (15/1/84)
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-e94effffd47c4e588833ae4b7fd9332b
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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