Piperidine → HCID 12666071, compound

HRID 848586Notes

Reaction equation

HRID 848586 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][CH2:22][CH2:21][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[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 12666069HCID 12666069, compound

Product 1

HCID 12666071HCID 12666071, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 8-chloro-4,5-dihydro-1-methyl-6H-s-triazolo[4,3-a][1,4]benzodiazepine-6-thione (VIIIa) (2.65 g., 0.01 mole) and piperidine (25 ml.) was refluxed for 18 hours, under nitrogen. The solution was mixed with cold water and extracted with methylene chloride. The extract was washed with water, then brine, dried (Na2SO4) and concentrated in vacuo. The solid residue was mixed with ethyl acetate and collected by filtration; it was recrystallized from a methylene chloride/methanol/ethyl acetate mixture to give 1.39 g., melting point 238°-243° (soften 235) and 0.40 g., melting point 225°-232° (soften 220) of the titled compound (Ia) (57% yield). The analytical sample had: melting point 248°-249.5° (soften 235°), uv (EtOH) λ max 214 mμ (ε34,850), 235 (sh, 13,200), 287 (sh, 2950), 293 (3050). The ir and nmr spectra support the proposed structure.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialbrine, dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. additionThe solid residue was mixed with ethyl acetate
  6. filtrationcollected by filtration
  7. customit was recrystallized from a methylene chloride/methanol/ethyl acetate mixture
  8. customto give 1.39 g

Sources & evidence

ORD record
ord-95ec1de3a1e741f6805e32088c5ee616
Source dataset
uspto-grants-1981_10
Patent number
US04296239

Reaction notes

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