9-chloro-7-(2-chlorophenyl)-2-methyl-5H-pyrimido[5,4-d][2]benzazepine → 9-Chloro-7-(2-chlorophenyl)-4,5,6,7-tetrahydro-2-methyl-1H-pyrimido[5,4-d][2]benzazepine, hydrochloride salt

HRID 464529Notes

Reaction equation

HRID 464529 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:21]=[C:20]([CH3:22])[N:19]=[CH:18][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.[H][H]>C(O)(=O)C.[Pt]=O>[ClH:1].[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[NH:21][C:20]([CH3:22])=[N:19][CH2:18][C:7]=3[CH2:8][NH:9][CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 132255009-chloro-7-(2-chlorophenyl)-2-methyl-5H-pyrimido[5,4-d][2]benzazepineHCID 178418361HCID 178418361, compound

Product 1

HCID 1317143529-Chloro-7-(2-chlorophenyl)-4,5,6,7-tetrahydro-2-methyl-1H-pyrimido[5,4-d][2]benzazepine, hydrochloride salt

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3.8 g (10.7 mmole) of 9-chloro-7-(2-chlorophenyl)-2-methyl-5H-pyrimido[5,4-d][2]benzazepine in 50 ml of acetic acid was hydrogenated at room temperature and atmospheric pressure in the presence of 0.5 g of prehydrogenated platinum oxide. After 3 hours about 500 ml (ca 2 equivalent) of hydrogen was absorbed and the catalyst was separated by filtration. The filtrate was concentrated at reduced pressure to dryness. The residue was dissolved in methylene chloride, washed with an excess of dilute ice cold sodium hydroxide, and dried over anhydrous sodium sulfate. The methylene chloride solution was diluted with an excess of methanolic hydrogen chloride and concentrated at reduced pressure. The residue was triturated with isopropanol and the crude product was collected by filtration. Recrystallization from methanol gave the pure product, m.p. 275°-276° C.

Workup

  1. customwas hydrogenated at room temperature
  2. customthe catalyst was separated by filtration
  3. concentrationThe filtrate was concentrated at reduced pressure to dryness
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed with an excess of dilute ice cold sodium hydroxide
  6. dry with materialdried over anhydrous sodium sulfate
  7. additionThe methylene chloride solution was diluted with an excess of methanolic hydrogen chloride
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was triturated with isopropanol
  10. filtrationthe crude product was collected by filtration
  11. customRecrystallization from methanol
  12. customgave the pure product, m.p. 275°-276° C.

Sources & evidence

ORD record
ord-53c926fe18364e22b3a02f2974ec2ab3
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

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