1,2,3,6-Tetrahydropyridine → HCID 12666078, compound

HRID 848587Notes

Reaction equation

HRID 848587 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH2:9][NH:8][C:7](=S)[C:6]=2[CH:17]=1.[NH:18]1[CH2:23][CH:22]=[CH:21][CH2:20][CH2:19]1>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([N:18]3[CH2:19][CH:20]=[CH:21][CH2:22][CH2:23]3)[C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 127501,2,3,6-TetrahydropyridineHCID 12666069HCID 12666069, compound

Product 1

HCID 12666078HCID 12666078, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 8-Chloro-4,5-dihydro-1-methyl-6H-s-triazolo[4,3-a][1,4]benzodiazepine-6-thione (2.65 g., 0.01 mole) and 1,2,3,6-tetrahydropyridine (15 ml.) was refluxed for 32 hours with a slow stream of nitrogen passing through the mixture. It was then kept at ambient temperature for three days, mixed with water and extracted with methylene chloride; the aqueous layer was saturated with sodium chloride and re-extracted with methylene chloride. The combined extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was crystallized from methylene chloride/ethyl acetate to give 3.41 g. of crude product. This material was chromatographed over silica gel (180 g.) with 5% methanol in methylene chloride. The first material eluted from the column was crystallized from a methylene chloride/ethyl acetate/Skellysolve® B mixture to give 0.37 g., melting point 224°-225.5° of the titled compound (Ib). The analytical sample was recrystallized from a methylene chloride/ethyl acetate and had melting point 224°-225°.

Workup

  1. temperaturewas refluxed for 32 hours with a slow stream of nitrogen passing through the mixture
  2. extractionextracted with methylene chloride
  3. extractionre-extracted with methylene chloride
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was crystallized from methylene chloride/ethyl acetate
  8. customto give 3.41 g
  9. customThis material was chromatographed over silica gel (180 g.) with 5% methanol in methylene chloride
  10. washThe first material eluted from the column
  11. customwas crystallized from a methylene chloride/ethyl acetate/Skellysolve® B mixture
  12. customto give 0.37 g

Sources & evidence

ORD record
ord-6d4669d4bd674841b1aabb7063fceedf
Source dataset
uspto-grants-1981_10
Patent number
US04296239

Reaction notes

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