Hydrochloric Acid → HCID 53659154, compound

HRID 1698774Notes

Reaction equation

HRID 1698774 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:13]2[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]2)[CH2:4][C@H:3]1[NH:19]C(OCCCC)=O.[N+](C1C=CC=CC=1)([O-])=O.Cl.C(=O)([O-])O.[Na+]>C1(C)C(C)=CC=CC=1.[C].[Pd].O.CO>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:4][C@H:3]1[NH2:19]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7416NitrobenzeneHCID 516892Sodium BicarbonateHCID 57016129HCID 57016129, compound

Product 1

HCID 53659154HCID 53659154, compoundYield 60.9%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (3R)-2-oxo-3-butoxycarbonylamino-5-(2-cyclohexen-1-yl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin e (12.87 g) in xylene (200 mL), nitrobenzene (22.16 g) and 10% palladium carbon (6 g) were added, followed by refluxing for 1 hour and 30 minutes. The reaction mixture was allowed to cool down and then filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (30mL), and a 4 N hydrochloric acid-dioxane solution (20 mL) was added, followed by stirring at 50° C. for 1 hour. After the reaction mixture was allowed to cool down, crystals so precipitated were collected by filtration and washed with 2-propanol, whereby the hydrochloride of the title compound was obtained. The hydrochloride was then dissolved under heat in a mixed solution of methanol and water. After the reaction mixture was allowed to cool down, a saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture for neutralization. Crystals so precipitated were collected by filtration, washed with water and then dried, whereby the title compound (5.55 g) was obtained.

Workup

  1. temperatureby refluxing for 1 hour and 30 minutes
  2. temperatureto cool down
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethanol (30mL)
  6. additiona 4 N hydrochloric acid-dioxane solution (20 mL) was added
  7. temperatureto cool down
  8. customcrystals so precipitated
  9. filtrationwere collected by filtration
  10. washwashed with 2-propanol, whereby the hydrochloride of the title compound
  11. customwas obtained
  12. temperatureto cool down
  13. customCrystals so precipitated
  14. filtrationwere collected by filtration
  15. washwashed with water
  16. customdried

Sources & evidence

ORD record
ord-44e994ece9af415c82660891d9940d9f
Source dataset
uspto-grants-2002_02
Patent number
US06344452B1

Reaction notes

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