Dimethylamine → 2-[2-(Dimethylamino)propyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one dihydrochloride

HRID 4850Notes

Reaction equation

HRID 4850 reaction equation
[I-].[Na+].[Cl:3][CH:4]([CH3:19])[CH2:5][CH:6]1[CH2:12][N:11]([CH3:13])[C:10](=[O:14])[C:9]2[CH:15]=[CH:16][CH:17]=[N:18][C:8]=2[O:7]1.[CH3:20][NH:21][CH3:22]>>[ClH:3].[ClH:3].[CH3:20][N:21]([CH3:22])[CH:4]([CH3:19])[CH2:5][CH:6]1[CH2:12][N:11]([CH3:13])[C:10](=[O:14])[C:9]2[CH:15]=[CH:16][CH:17]=[N:18][C:8]=2[O:7]1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 137264752-(2-chloropropyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one

Product 1

HCID 137266392-[2-(Dimethylamino)propyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one dihydrochloride

Procedure

Into a stainless steel bomb was placed 1.0 g sodium iodide, 5.0 g (0.017 mole) of 2-(2-chloropropyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one and 40 ml of dimethylamine. The bomb was sealed tightly, placed in the oven at 60° C. and rolled continuously for 7 days. The bomb was allowed to stand at room temperature for several days. The residue was combined with that of a previous run of equal size and separated via column chromatography using silica gel and eluting with ethanol and then with 3% triethylamine/ethanol. The fractions containing the desired product were combined and concentrated by rotary evaporation (80° C., 30 mm). The residue was taken up in 150 ml of chloroform and washed with 2×50 ml diluted sodium hydroxide. The chloroform was removed by rotary evaporation (70° C., 30 mm) and the residue treated with ethereal hydrogen chloride and hydrogen chloride in isopropyl alcohol. The white crystals which were collected weighed 3 g (28%), m.p. 173°-76° C.

Workup

  1. customThe bomb was sealed tightly
  2. customplaced in the oven at 60° C.
  3. waitto stand at room temperature for several days
  4. customseparated via column chromatography
  5. washeluting with ethanol
  6. additionThe fractions containing the desired product
  7. concentrationconcentrated by rotary evaporation (80° C., 30 mm)
  8. washwashed with 2×50 ml diluted sodium hydroxide
  9. customThe chloroform was removed by rotary evaporation (70° C., 30 mm)
  10. additionthe residue treated with ethereal hydrogen chloride and hydrogen chloride in isopropyl alcohol
  11. customThe white crystals which were collected

Sources & evidence

ORD record
ord-d72b57dfc95c4cd685ec1dc1014cf8f3
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Reaction notes

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