p-Toluenesulfonic acid → 1,2-Dibenzoylhexahydro-5-[2-(4-pyridinyl)ethyl]-1H-1,2,5-triazepine

HRID 2292279Notes

Reaction equation

HRID 2292279 reaction equation
[C:1]([N:9]1[CH:15]=[CH:14][N:13]=[CH:12][CH2:11][N:10]1[C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)=[CH2:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(O)C>[C:1]([N:9]1[CH2:15][CH2:14][N:13]([CH2:25][CH2:24][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:12][CH2:11][N:10]1[C:16](=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 75024-VinylpyridineHCID 212772311,2-dibenzoyl-1H-1,2,5-triazepine

Product 1

HCID 143909141,2-Dibenzoylhexahydro-5-[2-(4-pyridinyl)ethyl]-1H-1,2,5-triazepine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 1,2-dibenzoyl-1H-1,2,5-triazepine (2.0 g), 4-vinylpyridine (1.42 g) and p-toluenesulfonic acid (1.21 g) in methanol (70 ml) was stirred and heated at 60° under a nitrogen atmosphere for 3 days. The foam, obtained after evaporation of the solvent, was mixed with dichloromethane and 10% sodium carbonate solution. The organic phase was washed with water until neutral washings were obtained and dried (Na2SO4). Evaporation of the solvent gave a foam, 2.25 g. The crude product was chromatographed on a column of silica gel; elution with ethanol-ethyl acetate-dichloromethane (1:4:5) giving a major component. A hydrochloride salt, 1/3 hydrate of the titled compound was formed in ethanol; wt. 1.2 g (38%), mp 247° dec.

Workup

  1. temperatureheated at 60° under a nitrogen atmosphere for 3 days
  2. customThe foam, obtained
  3. customafter evaporation of the solvent
  4. additionwas mixed with dichloromethane and 10% sodium carbonate solution
  5. washThe organic phase was washed with water until neutral washings
  6. customwere obtained
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent
  9. customgave a foam, 2.25 g
  10. customThe crude product was chromatographed on a column of silica gel
  11. washelution with ethanol-ethyl acetate-dichloromethane (1:4:5)
  12. customgiving a major component

Sources & evidence

ORD record
ord-f5531f3529684b7cbed3fc064129a0a4
Source dataset
uspto-grants-1989_01
Patent number
US04801706

Reaction notes

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