1,4-Dioxane hydrochloride → HCID 21201625, compound

HRID 1979292Notes

Reaction equation

HRID 1979292 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:7][C:6](=[N:21]OC(NCCC)=O)[C:5]1=[O:29].[ClH:30].O1CCOCC1>CO.CCOCC.[C].[Pd]>[ClH:30].[CH3:1][O:2][CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:7][CH:6]([NH2:21])[C:5]1=[O:29]

Participants

6

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 53975421HCID 53975421, compound

Product 1

HCID 21201625HCID 21201625, compoundYield 69.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

10% Palladium carbon (2.0 g) was added to 1-methoxymethyl-2-oxo-3-propylaminocarbonyloxyimino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (14.2 g) suspended in methanol (200 ml), and the resultant mixture was stirred for two hours under hydrogen atmosphere (3 kg/cm2) at room temperature. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1), to thereby obtain a yellow oily substance. The substance was dissolved in ether, and 4N hydrochloric acid-dioxane (10 ml) was added thereto. Crystals so precipitated were collected by filtration, to thereby obtain 8.28 g of the title compound as a white solid (yield: 69.3%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
  4. customto thereby obtain a yellow oily substance
  5. customCrystals so precipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-d48b36d8f8bd46bc8b0877f08d2158d0
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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