N,N-Dimethylethylenediamine → 3-(8-Chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)-4-[[2-(dimethylamino)ethyl]amino]-3-cyclobutene-1,2-dione, hydrochloride

HRID 1707578Notes

Reaction equation

HRID 1707578 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[O:6][C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=3[CH2:9][N:10]([C:11]3[C:12](=O)[C:13](=[O:18])[C:14]=3[O:15]CC)[C:4]=2[CH:3]=1.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][NH2:30]>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[O:6][C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=3[CH2:9][N:10]([C:11]3[C:14](=[O:15])[C:13](=[O:18])[C:12]=3[NH:30][CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 152322933-(8-Chloro-dibenz[b,f][1,4]oxazepin-10(11H)-yl)-4-ethoxy-3-cyclobutene-1,2-dione

Product 1

HCID 1317187273-(8-Chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)-4-[[2-(dimethylamino)ethyl]amino]-3-cyclobutene-1,2-dione, hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the title product of Example 5 (0.73 g), N,N-dimethylethylenediamine (0.225 mL) and dioxane (20 mL) was heated to reflux for 20 minutes. Then, most of the dioxane was removed in vacuo and the residue was stirred in methanol (20 mL) at ambient temperature for 1/2 hour and the precipitated white solid was filtered and discarded. The filtrate was concentrated and the residue was chromatographed on silica gel using 1% each of methanol and triethylamine in ethyl acetate to give the free amine of the title compound as a pale yellow solid. To a solution of this solid in CH2Cl2 (3 mL) was added 7 N HCl in dioxane (1 mL) and the mixture concentrated. To the residue was added excess water and the resulting mixture was freeze dried to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 minutes
  3. customThen, most of the dioxane was removed in vacuo
  4. filtrationthe precipitated white solid was filtered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was chromatographed on silica gel using 1% each of methanol and triethylamine in ethyl acetate

Sources & evidence

ORD record
ord-63aae56a6c4643bd90a869ea4b4f0084
Source dataset
uspto-grants-1994_10
Patent number
US05354746

Reaction notes

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