Methylamine → HCID 44265477, compound

HRID 1735590Notes

Reaction equation

HRID 1735590 reaction equation
CN.[CH2:3]([N:5](CC)CC)C.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:25]3[CH:26]=[C:27]4[O:32][CH2:31][O:30][C:28]4=[CH:29][C:24]=3[CH2:23][CH:22]([CH3:33])[N:21]([C:34](=[O:37])[CH2:35]Cl)[N:20]=2)=[CH:15][CH:14]=1)([O-])=O>C(O)C>[NH2:10][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:25]3[CH:26]=[C:27]4[O:32][CH2:31][O:30][C:28]4=[CH:29][C:24]=3[CH2:23][CH:22]([CH3:33])[N:21]([C:34](=[O:37])[CH2:35][NH:5][CH3:3])[N:20]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 11090693HCID 11090693, compound

Product 1

HCID 44265477HCID 44265477, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.03 g (15.3 mmol) of methylamine hydrocdhloride and 2.64 ml (18.3 mmol) of triethylamine were added to a suspension containing 1.23 g (3.06 mmol) of 1-(4-nitrophenyl)-3-chloroacetyl-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine in 140 ml of ethanol and the reaction mixture was refluxed for 10 hours, then evaporated under reduced pressure. The residue was dissolved in 30 ml of chloroform, washed with 20 ml of 4% NaOH solution, then 2×20 ml of water, dried and evaporated under reduced pressure. The residue was reduced according to the process of Example 16 and the product obtained was purified by column chromatography (adsorbent: Kieselgel 60, eluent: methanol--benzene 4:1). The crude product obtained was triturated with 5 ml of ethyl acetate at 25° C. to obtain 0.60 g (53.6%) of the aimed product, m.p. 198°-200° C. (weak decomp.).

Workup

  1. temperaturethe reaction mixture was refluxed for 10 hours
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 30 ml of chloroform
  4. washwashed with 20 ml of 4% NaOH solution
  5. dry with material2×20 ml of water, dried
  6. customevaporated under reduced pressure
  7. customthe product obtained
  8. customwas purified by column chromatography (adsorbent: Kieselgel 60, eluent: methanol--benzene 4:1)
  9. customThe crude product obtained
  10. customwas triturated with 5 ml of ethyl acetate at 25° C.

Sources & evidence

ORD record
ord-49ee289835b143d288b763428b7d4d67
Source dataset
uspto-grants-1996_07
Patent number
US05536832

Reaction notes

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