Triethylamine → HCID 21738595, compound

HRID 440816Notes

Reaction equation

HRID 440816 reaction equation
Cl.CN.[CH2:4]([N:6](CC)CC)C.Cl[CH2:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:28]3[CH:29]=[C:30]4[O:35][CH2:34][O:33][C:31]4=[CH:32][C:27]=3[CH2:26][CH:25]([CH3:36])[N:24]([C:37](=[O:39])[CH3:38])[N:23]=2)=[CH:18][CH:17]=1)=[O:14]>C(O)C>[CH3:4][NH:6][CH2:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:28]3[CH:29]=[C:30]4[O:35][CH2:34][O:33][C:31]4=[CH:32][C:27]=3[CH2:26][CH:25]([CH3:36])[N:24]([C:37](=[O:39])[CH3:38])[N:23]=2)=[CH:18][CH:17]=1)=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 53713423HCID 53713423, compound

Product 1

HCID 21738595HCID 21738595, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.31 g (19.5 mmol) of methylamine hydrochloride and 3.24 ml (23.3 mmol) of triethylamine were added to a suspension containing 1.61 g (3.89 mmol) of 1-(4-chloroacetylaminophenyl)-3-acetyl-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine (see Example 106) in 100 ml of ethanol and the reaction mixture was refluxed for 10 hours, then evaporated under reduced pressure. The residue was purified by column chromatography (adsorbent: Kieselgel 60, eluent: chloroform--methanol 9:1). The crude product was triturated with 3 ml of 50% ethanol at 25° C. to give 0.61 g (38.6%) of the aimed product, m.p.: 220°-222° C. (weak decomp.).

Workup

  1. temperaturethe reaction mixture was refluxed for 10 hours
  2. customevaporated under reduced pressure
  3. customThe residue was purified by column chromatography (adsorbent: Kieselgel 60, eluent: chloroform--methanol 9:1)
  4. customThe crude product was triturated with 3 ml of 50% ethanol at 25° C.

Sources & evidence

ORD record
ord-b6e0eac807f2427c8fb03a2816ce5a61
Source dataset
uspto-grants-1996_05
Patent number
US05521174

Reaction notes

Loading…