1,2-dibenzoyl-5-phenyl-1H-1,2,5-triazepine → 1,2-Dibenzoylhexahydro-1H-1,2,5-triazepine

HRID 2292276Notes

Reaction equation

HRID 2292276 reaction equation
[C:1]([N:9]1[CH:15]=[CH:14][N:13](C2C=CC=CC=2)[CH:12]=[CH:11][N:10]1[C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].O1CCOCC1>[C:1]([N:9]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][N:10]1[C:22](=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 212772361,2-dibenzoyl-5-phenyl-1H-1,2,5-triazepine

Product 1

HCID 143909121,2-Dibenzoylhexahydro-1H-1,2,5-triazepine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,2-dibenzoyl-5-phenyl-1H-1,2,5-triazepine (25.0 g), dioxane (500 ml), N-hydrochloric acid (250 ml) and 10% Palladium on carbon (1.3 g) was hydrogenated in a Parr apparatus at 16 p.s.i. pressure for 191/2 hours. The catalyst was removed by filtration and washed with water. The filtrate and washings were evaporated to a solid hydrochloride salt which was dried under oil pump vacuum; wt. 22.4 g. The material was assayed by HPLC and shown to be 91% pure. Material prepared in this way was used directly in further syntheses, e.g., in example 8.

Workup

  1. custom2 hours
  2. customThe catalyst was removed by filtration
  3. washwashed with water
  4. customThe filtrate and washings were evaporated to a solid hydrochloride salt which
  5. customwas dried under oil pump vacuum
  6. customMaterial prepared in this way

Sources & evidence

ORD record
ord-785ff56f60234e48a3669a962818a9f0
Source dataset
uspto-grants-1989_01
Patent number
US04801706

Reaction notes

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