Diphenyl Ether → 3-(8-Chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)-4-[(4-pyridinylmethyl)amino]-3-cyclobutene-1,2-dione, hydrochloride

HRID 1707579Notes

Reaction equation

HRID 1707579 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:19])[C:13](=[O:18])[C:14]=3OCC)[C:4]=2[CH:3]=1.[NH2:26][CH2:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[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:12](=[O:19])[C:13](=[O:18])[C:14]=3[NH:26][CH2:27][C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 773174-PyridinemethanamineHCID 152322933-(8-Chloro-dibenz[b,f][1,4]oxazepin-10(11H)-yl)-4-ethoxy-3-cyclobutene-1,2-dione

Product 1

HCID 1317187283-(8-Chlorodibenz[b,f][1,4]oxazepin-10(11H)-yl)-4-[(4-pyridinylmethyl)amino]-3-cyclobutene-1,2-dione, hydrochloride

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of the product of Example 5 (0.75 g), 4-(aminomethyl)pyridine (0.14 mL) and diphenylether (2 mL) was heated to reflux for 3 hours. The mixture was cooled and added to hexane (200 mL) and the separated thick oil was recovered by decantation. The oil was triturated with methanol. The precipitated solid was filtered and stirred with methanol at ambient temperature for 16 hours. The solid was then filtered and dissolved in CHCl3 (4 mL). To the solution was added 7 N HCl (1 mL) and the mixture was concentrated in vacuo. The residue was triturated with ether and filtered to obtain the title compound as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. customthe separated thick oil was recovered by decantation
  5. customThe oil was triturated with methanol
  6. filtrationThe precipitated solid was filtered
  7. filtrationThe solid was then filtered
  8. dissolutiondissolved in CHCl3 (4 mL)
  9. additionTo the solution was added 7 N HCl (1 mL)
  10. concentrationthe mixture was concentrated in vacuo
  11. customThe residue was triturated with ether
  12. filtrationfiltered

Sources & evidence

ORD record
ord-6e5783f4c61f4820a2ea8773fab478b1
Source dataset
uspto-grants-1994_10
Patent number
US05354746

Reaction notes

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