HCID 13631910, compound → HCID 13631928, compound

HRID 1905632Notes

Reaction equation

HRID 1905632 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:16][C:15](=[O:17])[C:9]3([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)[N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1.C(O)(C)C.Cl.[H][H]>CO.[Pt]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:16][C:15](=[O:17])[C:9]3([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)[NH:8][CH:7]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:6]=2[CH:24]=1

Participants

6

Reactant 3

HCID 13631910HCID 13631910, compoundHCID 21912024Isopropanol hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 13631928HCID 13631928, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

4.0 g (0.012 mole) of 7-chloro-5-phenyl-spiro[1H-1,4-benzodiazepine-3,4'-piperidin]-2(3H)-one are hydrogenated in 160 ml of methanol with the addition of 10 ml of a 30% strength isopropanol/HCl solution in the presence of platinum at 25° C. in the course of 3 hours, until the calculated amount of hydrogen has been taken up. After filtration, the solvent is distilled off, the residue is rendered alkaline with aqueous concentrated ammonia solution and the base is extracted by shaking with methylene chloride. The organic phase is washed with water, dried over Na2SO4 and concentrated and the residue is chromatographed on silica gel 60 (Merck); eluting agent: methylene chloride/methanol/25% strength aqueous ammonia solution (14:2.5:0.5).

Workup

  1. filtrationAfter filtration
  2. distillationthe solvent is distilled off
  3. extractionthe base is extracted
  4. washThe organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customthe residue is chromatographed on silica gel 60 (Merck)
  8. washeluting agent

Sources & evidence

ORD record
ord-b796b893ecea4304ba291c1770988f43
Source dataset
uspto-grants-1987_03
Patent number
US04647560

Reaction notes

Loading…